Hydroxylamine → Methyl 5-[amino(hydroxyimino)methyl]-2-chlorobenzoate

HRID 219856Notes

Reaction equation

HRID 219856 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH2:14][OH:15]>CCO>[NH2:13][C:12](=[N:14][OH:15])[C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 16659388Methyl 2-chloro-5-cyanobenzoate

Product 1

HCID 72307491Methyl 5-[amino(hydroxyimino)methyl]-2-chlorobenzoateYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-chloro-5-cyanobenzoate (1.55 g; 7.92 mmol; 1 eq.) was suspended in EtOH (31 mL). Hydroxylamine (1.17 mL; 39.62 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 6 hours. The mixture was concentrated affording the title compound as a beige solid (1.65 g, 91%). 1H NMR (DMSO-d6, 300 MHz) δ 9.92 (br s, 1H), 8.19-8.18 (m, 1H), 7.92-7.90 (m, 1H), 7.68-7.65 (m, 1H), 6.04 (br s, 2H), 3.95 (s, 3H). LC/MS (Method B): 229.0 (M+H)+; 227.0 (M−H)−.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-52767a77c5f340d383cdd4cc4b9ce6df
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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