Hydroxyamine hydrochloride → 3-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline

HRID 452563Notes

Reaction equation

[CH3:1][N:2]([CH3:17])[C:3]1[CH:4]=[C:5]([C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)=O)[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[OH:20][N:19]=[C:9]([C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1)[C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[N:2]([CH3:17])[CH3:1]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of [3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methanone (3.84 g, 17 mmol) in dry pyridine (30 mL) was added hydroxylamine hydrochloride (2.89 g, 42 mmol). The reaction mixture was stirred at 70° C. for 6 h, then concentrated in vacuo and diluted with ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with water (50 mL) and dried over MgSO4. Evaporation of the solvent in vacuo afforded 3-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline as a yellow solid [4.48 g, yield 99.6%; HPLC/MS:m/z=247 (M+H); log P(HCOOH)=1.17].

Workup

concentrationconcentrated in vacuo
additiondiluted with ethyl acetate (100 mL) and water (50 mL)
customThe organic layer was separated
washwashed with water (50 mL)
dry with materialdried over MgSO4
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-1b54bdb5e0ea46d08a9d0e1c4b66fa7d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492388B2

Reaction notes

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