Hydroxyamine hydrochloride → N-hydroxy-1-[3-(methoxymethyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

HRID 452570Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)=O)[CH:7]=[CH:8][CH:9]=1.Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[OH:20][N:19]=[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=1)[C:12]1[N:16]([CH3:17])[N:15]=[N:14][N:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of [3-(methoxymethyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone (7.17 g, 31 mmol) in dry pyridine (50 mL) was added hydroxylamine hydrochloride (5.36 g, 77 mmol). The reaction mixture was stirred at 70° C. for 4 h, then concentrated in vacuo and diluted with ethyl acetate (200 mL) and water (100 mL). The organic layer was separated, washed with water (100 mL) and dried (MgSO4). Evaporation of the solvent in vacuo afforded N-hydroxy-1-[3-(methoxymethyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as a yellow oil [8.43 g, yield 99.5%; HPLC/MS:m/z=248 (M+H); log P(HCOOH)=1.54].

Workup

concentrationconcentrated in vacuo
additiondiluted with ethyl acetate (200 mL) and water (100 mL)
customThe organic layer was separated
washwashed with water (100 mL)
dry with materialdried (MgSO4)
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-07d4aa6ec66b4381acd39db0f638caf0
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492388B2

Reaction notes

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