Hydroxyamine hydrochloride → 6-Amino-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

HRID 1507606Notes

Reaction equation

[CH:1]1([N:4]2[C:12]3[CH:11]=[C:10]([N:13]=C(C4C=CC=CC=4)C4C=CC=CC=4)[N:9]=[CH:8][C:7]=3[C:6]([CH3:28])([CH3:27])[C:5]2=[O:29])[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].Cl.NO>CO>[NH2:13][C:10]1[N:9]=[CH:8][C:7]2[C:6]([CH3:28])([CH3:27])[C:5](=[O:29])[N:4]([CH:1]3[CH2:2][CH2:3]3)[C:12]=2[CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1-cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (2.31 g, 6.06 mmol), sodium acetate (1.49 g, 18.2 mmol) and hydroxylamine hydrochloride (926 mg, 13.3 mmol) in methanol (60 ml) was heated to 50° C. for 3 hours. The reaction mixture was diluted with methanol, silica gel was added and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel using dichloromethane/methanol as eluent. The title compound was obtained as off-white crystals (1.1 g).

Workup

additionwas added
customthe solvent was evaporated
customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-b091d6ca87c74efbb8f8645b4f1922e5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221816B2

Reaction notes

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