Water → HCID 178520043, compound

HRID 1862167Notes

Reaction equation

HRID 1862167 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[N:13]([O-])=O.[Na+].[OH2:17]>>[CH:2]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][CH:5]=2)[NH:1][N:13]=1)=[O:17]

Participants

4

Reactant 3

HCID 962WaterHCID 5952301H-indole-6-carboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 178520043HCID 178520043, compoundYield 100%

Procedure

To 1H-indole-6-carboxylic acid (2.0 g, 12.42 mmol) in water (100 mL) was added NaNO2 (8.56 g, 124.2 mmol). To this suspension was then slowly added dropwise via addition funnel 6N HCL (16 mL). The resulting slurry was allowed to stir at room temperature overnight. The solid precipitate was filtered and washed with water (50 mL) to provide 2.35 g (100%) of 3-formyl-1H-indazole-6-carboxylic acid. 1H NMR (DMSO-d6) δ 14.46 (1H, s), 10.21 (1H, s), 8.26 (1H, s), 8.20 (1H, d, J=8.5Hz), 7.90 (1H, d, J=8.3 Hz). MS (APCI positive) 205 (methyl ester).

Workup

  1. additionTo this suspension was then slowly added dropwise via addition funnel 6N HCL (16 mL)
  2. filtrationThe solid precipitate was filtered
  3. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-a1872bf93e9d4924b26d9318368a3289
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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