Hydroxyamine hydrochloride → 1-(2-Chlorobenzyl)-3-(1-hydroxyiminoethyl)-2-propylindole-6-carboxamide

HRID 1108747Notes

Reaction equation

[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH2:15])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:5]=1[CH2:24][CH2:25][CH3:26])(=O)[CH3:2].Cl.[NH2:28][OH:29].C([O-])(=O)C.[Na+]>C(O)C>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([C:13]([NH2:15])=[O:14])[CH:8]=2)[C:4]([C:1](=[N:28][OH:29])[CH3:2])=[C:5]1[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxamide (36.5 mg) in ethanol (5 ml) was added hydroxylamine hydrochloride (70 mg) and sodium acetate (200 mg), and the mixture was heated in a sealed tube at 100° C. The reaction was evaporated in vacuo, then the residue was diluted with ethyl acetate and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 1-(2-chlorobenzyl)-3-(1-hydroxyiminoethyl)-2-propylindole-6-carboxamide (32.7 mg).

Workup

customThe reaction was evaporated in vacuo
additionthe residue was diluted with ethyl acetate
washwashed with water and brine
dry with materialThe organic phase was dried over sodium sulfate
customevaporated in vacuo
customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-11a9a403f247433cad2a8b8efa525c46
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069156

Reaction notes

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