Ethanol → [3-Amino-5-(trifluoromethyl)phenyl]propan-2-ol

HRID 1640136Notes

Reaction equation

CC1[N:3]([C:8]2[CH:9]=[C:10]([C:18](O)([CH3:20])C)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)C(C)=CC=1.Cl.NO.[OH-:25].[K+].[CH3:27]CO>O>[NH2:3][C:8]1[CH:9]=[C:10]([CH2:18][CH:20]([OH:25])[CH3:27])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)phenyl]-propan-2-ol (2.29 g, 7.70 mmol) in EtOH (70 mL) and water (41 mL), was added hydroxylamine hydrochloride (16.1 g, 23.1 mmol) and potassium hydroxide (8.64 g, 154 mmol). The reaction mixture was heated at 110° C. for 18 h, and then allowed to cool to rt. The solvents were evaporated and the residue was dissolved in water and extracted with EtOAc (2×). The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and evaporated. The residue was triturated with Et2O and the filtrate was evaporated to provide -[3-amino-5-(trifluoromethyl)phenyl]propan-2-ol (1.70 g, quant). 1H NMR (400 MHz,CDCl3) δ: 7.08 (s, 1H), 6.99 (s, 1H), 6.79 (s, 1H), and 1.56 (s, 6H).

Workup

temperatureto cool to rt
customThe solvents were evaporated
dissolutionthe residue was dissolved in water
extractionextracted with EtOAc (2×)
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe residue was triturated with Et2O
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-d56dcec75bf04d02ba1132a1adbe0864
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110687B2

Reaction notes

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