Hydroxylamine → HCID 76685370, compound

HRID 2410560Notes

Reaction equation

HRID 2410560 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:5]([C:20]([F:23])([F:22])[F:21])[CH:4]=1)#[N:2].[NH2:24][OH:25]>C(O)C>[OH:25][N:24]=[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[C:5]([C:20]([F:21])([F:23])[F:22])[CH:4]=1)[NH2:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66677560HCID 66677560, compound

Product 1

HCID 76685370HCID 76685370, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-((4-cyano-2-(trifluoromethyl)benzyl)(methyl)amino)acetate (0.541 g, 1.65 mmol) and 50% aqueous hydroxylamine (0.50 mL) in ethanol (2 mL) was heated at 75° C. for 2 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was passed through a hydrophobic frit and evaporated in vacuo to afford the title compound (0.460 g, 77%). 1H NMR (CDCl3, 400 MHz,) δ 7.97 (1H, d, J=8.1 Hz), 7.89 (1H, s), 7.78 (1H, d, J=8.1 Hz), 4.86 (2H, br s), 3.86 (2H, s), 3.23 (2H, s), 2.37 (3H, s), 1.48 (9H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-ece71b023e5c440cb0d4339a53bf2985
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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