Hydroxylamine → HCID 59022874, compound

HRID 1395884Notes

Reaction equation

HRID 1395884 reaction equation
[OH-:1].[Na+].O[NH2:4].C[O:6][C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][CH:10]=1)=O>C1COCC1.CO.O>[OH:1][NH:4][C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][CH:10]=1)=[O:6]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 109785681-cyclohexylmethyl-1H-indole-6-carboxylic acid methyl ester

Product 1

HCID 59022874HCID 59022874, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of sodium hydroxide (0.1 g, 2.5 mmol) and 50% aqueous hydroxyl amine (1 mL) was added 1-cyclohexylmethyl-1H-indole-6-carboxylic acid methyl ester (0.2 g, 0.7 mmol) dissolved in THF/MeOH (2 mL, 1:1). After stirring 3.5 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-cyclohexylmethyl-1H-indole-6-carboxylic acid hydroxyamide as a white solid (0.16 g, 84% yield). 1H NMR (400 MHz, DMSO) δ 11.13 (s, 1H), 8.92 (s, 1H), 7.92 (s, 1H), 7.55 (d, 1H, J=8.0 Hz), 7.47-7.42 (m, 2H), 6.45 (d, 11, J=3.1 Hz), 4.03 (d, 2H, J=7.4 Hz), 1.84 (m, 1H), 1.66-1.57 (m 3H), 1.47 (m, 2H), 1.12 (m, 3H), 0.98 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-d73a6dc2f6244ac5a8088e0fedf15742
Source dataset
uspto-grants-2014_12
Patent number
US08900565B2

Reaction notes

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