Hydroxyamine hydrochloride → HCID 178498207, compound

HRID 536434Notes

Reaction equation

HRID 536434 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](C=O)=[C:9]2[C:13]=1[N:12]([CH3:14])[N:11]=[CH:10]2)=[O:4].Cl.[NH2:18][OH:19].[C:20]([O-])(=O)C.[Na+]>C(O)(C)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](=[N:18][OH:19])[C:9]2[C:13]=1[N:12]([CH3:14])[NH:11][C:10]=2[CH3:20])=[O:4]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 58524124HCID 58524124, compound

Product 1

HCID 178498207HCID 178498207, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 4-formyl-1-methyl-1H-indazole-7-carboxylic acid methyl ester (1.4 g) in isopropyl alcohol (30 ml) and water (20 ml) was treated with hydroxylamine hydrochloride (0.62 g) and sodium acetate (0.72 g) and stirred for 4 h. Isopropyl alcohol was removed and the remaining mixture was extracted with ethyl acetate (2×50 ml). The combined organic layers were dried over sodium sulfate and concentrated to give 4-(hydroxyimino-methyl-1-methyl-1H-indazole-7-carboxylic acid methyl ester (1.5 g). 1H-NMR (400 MHz, DMSO): 10.1 (s, 1H), 8.5 (s, 1H), 8.4 (s, 1H), 7.8 (d, 1H), 7.1 (d, 1H), 4.20 (s, 3H), 4.00 (s, 3H).

Workup

  1. customIsopropyl alcohol was removed
  2. extractionthe remaining mixture was extracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a268dadca5cc48cfaca9be93d82f97e9
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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