Methanol → HCID 178499646, compound

HRID 1461466Notes

Reaction equation

HRID 1461466 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[N:2]1.[CH3:14]O>S(=O)(=O)(O)O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 178525248HCID 178525248, compound

Product 1

HCID 178499646HCID 178499646, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 1H-indazole-3-acetic acid (1.0 g) prepared according to J. Am. Chem. Soc., 79, 5245 (1957), in methanol (30 ml) containing five drops of concentrated sulfuric acid was refluxed for 8 hours. The reaction mixture was then concentrated to a low volume and diluted with ethyl acetate (20 ml). The organic layer was washed with water (2×10 ml) and then with sodium bicarbonate solution (10 ml, 10%). The ethyl acetate layer was collected and then dried to obtain the title compound (yield: 0.8 g; m.p. 146° C.).

Workup

  1. temperaturewas refluxed for 8 hours
  2. concentrationThe reaction mixture was then concentrated to a low volume
  3. additiondiluted with ethyl acetate (20 ml)
  4. washThe organic layer was washed with water (2×10 ml)
  5. customThe ethyl acetate layer was collected
  6. customdried

Sources & evidence

ORD record
ord-2faff251b83b4c28b4a5a1fdc5e04f27
Source dataset
uspto-grants-1991_12
Patent number
US05075442

Reaction notes

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