Water → HCID 178520043, compound

HRID 724440Notes

Reaction equation

HRID 724440 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=8.5 Hz), 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-8ee6d6ec7acc4ce6978e995e41319b9a
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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