Hydroxylamine → N'-Hydroxy-4-(hydroxymethyl)benzene-1-carboximidamide

HRID 572579Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[NH2:11][OH:12]>CCO>[OH:12][N:11]=[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1)[NH2:8]

Participants

Conditions

Temperature: 74 °C

Procedure

To a solution of 4-(hydroxymethyl)benzonitrile (11.05 g; 83.08 mmol) in EtOH (100 mL) was added hydroxylamine (27.4 mL; 415 mmol) (50% in water) and the mixture was heated to 74° C. for 16 hours. The mixture was poured into a crystallizing dish and the solvent were evaporated. The residue was washed with copious amounts of EtOAc, dry MeOH and dry MeCN which was filtered through a hydrophobic frit and the solvent removed in vacuo to give the title compound as a white solid (13.1 g, 95%). 1H NMR (DMSO-d6, 400 MHz) δ 9.58 (s, 1H), 7.70-7.62 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 5.79 (s, 2H), 5.23 (t, J=5.6 Hz, 1H), 4.54 (d, J=5.6 Hz, 2H).

Workup

additionThe mixture was poured into a crystallizing dish
customthe solvent were evaporated
washThe residue was washed with copious amounts of EtOAc, dry MeOH and dry MeCN which
filtrationwas filtered through a hydrophobic frit
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-004a0da70f5c445caa68cbe324e7e6fc
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029405B2

Reaction notes

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