Hydroxyamine hydrochloride → HCID 58551635, compound

HRID 2204263Notes

Reaction equation

[CH2:1]([C:3]1[CH:30]=[CH:29][C:6]([C:7]([N:9]2[CH2:14][CH2:13][C:12]3([O:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[N:16]4[C:24]([CH:27]=O)=[CH:25][CH:26]=[C:15]34)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[O:31][CH3:32])[CH3:2].Cl.[NH2:34][OH:35].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([C:3]1[CH:30]=[CH:29][C:6]([C:7]([N:9]2[CH2:14][CH2:13][C:12]3([O:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[N:16]4[C:24](/[CH:27]=[N:34]\[OH:35])=[CH:25][CH:26]=[C:15]34)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[O:31][CH3:32])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 1′-(4-ethyl-3-methoxybenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbaldehyde (950 mg, 2.21 mmol) in ethanol (4.7 mL) was heated at 60° C. A solution of hydroxylamine hydrochloride (693 mg, 9.97 mmol) and sodium acetate (1.38 g, 16.8 mmol) in water (4.7 mL) was added to the carbaldehyde solution. The reaction mixture was heated at 70° C. for 30 minutes before it was cooled to room temperature. Water was added and the product formed a white precipitate which was collected by filtration. The solids were washed with water and toluene, and dried under reduced pressure to give (Z)-1′-(4-ethyl-3-methoxybenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbaldehyde oxime (847 mg).

Workup

temperaturewas cooled to room temperature
customthe product formed a white precipitate which
filtrationwas collected by filtration
washThe solids were washed with water and toluene
customdried under reduced pressure

Sources & evidence

ORD record: ord-92ff0b7463d64e73a5e461381452aff5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365588B2

Reaction notes

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