How can INSERT INTO a table 300 times within a loop in SQL?

You may try it like this:

DECLARE @i int = 0
WHILE @i < 300 
BEGIN
    SET @i = @i + 1
    /* your code*/
END

DECLARE @first AS INT = 1
DECLARE @last AS INT = 300

WHILE(@first <= @last)
BEGIN
    INSERT INTO tblFoo VALUES(@first)
    SET @first += 1
END

I would prevent loops in general if i can, set approaches are much more efficient:

INSERT INTO tblFoo
  SELECT TOP (300) n = ROW_NUMBER()OVER (ORDER BY [object_id]) 
  FROM sys.all_objects ORDER BY n;

Demo

Generate a set or sequence without loops