Hydroxylamine → N-Hydroxy-1-[(4-methoxyphenyl)methyl]-1H-indole-6-carboxamide

HRID 2195730Notes

Reaction equation

HRID 2195730 reaction equation
[OH-:1].[Na+].[NH2:3]O.C[O:6][C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)=O>C1COCC1.CO.O>[OH:1][NH:3][C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)=[O:6]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 69451957HCID 69451957, compound

Product 1

HCID 24753719N-Hydroxy-1-[(4-methoxyphenyl)methyl]-1H-indole-6-carboxamideYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of sodium hydroxide (0.2 g, 5 mmol) and 50% aqueous hydroxylamine (2 mL) was added 1-(4-methoxy-phenylmethyl)-1H-indole-6-carboxylic acid methyl ester (0.32 g, 1.0 mmol) dissolved in THF/MeOH (4 mL, 1:1). After stirring 1 hr at room temperature, the solution was diluted with water (4 mL) and the volatile solvents were removed in vacuo. The solution was then neutralized to pH=7-8 with 1N HCl. The resulting precipitate was isolated by filtration to provide 1-(4-methoxy-phenylmethyl)-1H-indole-6-carboxylic acid hydroxyamide as a white powder (0.25 g, 84% yield). 1H NMR (400 MHz, DMSO) δ 11.13 (s, 1H), 8.93 (s, 1H), 7.97 (s, 1H), 7.64 (d, 1H, J=3.2 Hz), 7.58 (d, 1H, J=8.9 Hz), 7.45 (d, 1H, J=8.3 Hz), 7.19 (d, 2H, J=8.3 Hz), 6.87 (d, 2H, J=8.3 Hz), 6.52 (d, 1H, J=3.2 Hz), 5.38 (s, 2H), 3.70 (s, 3H).

Workup

  1. customthe volatile solvents were removed in vacuo
  2. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-fb4fda2ac438475e9671470edce30c5b
Source dataset
uspto-grants-2012_12
Patent number
US08338416B2

Reaction notes

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