Hydroxyamine hydrochloride → HCID 178426650, compound
Reaction equation
C[C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.[NH2:20][OH:21].[C:22](=O)(O)[O-].[Na+]>CO>[OH:21][NH:20][C:8](=[NH:9])[C:7]1[CH:2]=[CH:3][C:4]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[C:5]([CH3:22])[CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2.5 g (10.2 mmol) of tert-butyl 3-(3-methyl-4-cyanophenyl) propionate (from Step B), 0.85 g (12.2 mmol) of hydroxylamine hydrochloride and 2.57 g (30.6 mmol) of sodium bicarbonate in 30 mL of methanol was heated in a sealed tube at 100° C. for 16 h. The reaction mixture was cooled to rt, then concentrated. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated and washed with sat'd NaCl (3×50 mL), dried over MgSO4, and concentrated. Chromatography on a Biotage 40M cartridge using 7:3 v/v hexanes/EtOAc as the eluant afforded 1.65 g (58%) of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.45 (s, 9H), 2.40 (s, 3H), 2.54 (t, J=7.8, 2H), 2.90 (t, J=7.8, 2H), 5.05 (s, 2H), 7.04 (d, J=7.8, 1H), 7.08 (s, 1H), 7.27 (d, J=7.8, 1H).
Workup
- temperatureThe reaction mixture was cooled to rt
- concentrationconcentrated
- customThe residue was partitioned between EtOAc (50 mL) and water (50 mL)
- customThe organic layer was separated
- washwashed with sat'd NaCl (3×50 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6fa6cca7acb049bfa10d5b26f69e060e
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605171B2
Reaction notes
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