Hydroxylamine → Methyl 4-[amino(hydroxyimino)methyl]-2-chloro-5-fluorobenzoate

HRID 219859Notes

Reaction equation

HRID 219859 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:9]([F:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH2:15][OH:16]>CCO>[NH2:13][C:12](=[N:15][OH:16])[C:10]1[C:9]([F:14])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([Cl:1])[CH:11]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67528656Methyl 2-chloro-4-cyano-5-fluorobenzoate

Product 1

HCID 72307477Methyl 4-[amino(hydroxyimino)methyl]-2-chloro-5-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-chloro-4-cyano-5-fluorobenzoate (1.65 g; 7.72 mmol; 1 eq.) was suspended in EtOH (33 mL). Hydroxylamine (1.14 mL; 38.62 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 6 hours. The obtained suspension was filtered affording the title compound as a beige solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.98 (br s, 1H), 7.74-7.67 (m, 2H), 6 (hr s, 2H), 3.87 (s, 3H). LC/MS (Method B): 247.0 (M+H)+; 245.1 (M−H)−. HPLC (Method A) Rt 1.80 min (Purity: 90.4%).

Workup

  1. filtrationThe obtained suspension was filtered

Sources & evidence

ORD record
ord-71f670b3d5c04912a3fc3057393be355
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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