Hydrochloric Acid → HCID 57567369, compound

HRID 2404796Notes

Reaction equation

[C:1]([C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[C:7]#[N:8])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1.CO.Cl>C1COCC1.O>[C:1]([C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[CH2:7][NH2:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-tert-butyl-5-nitrobenzonitrile (612 mg, 3.0 mmol) in THF (10 mL) was added a solution of BH3.THF (12 mL, 1M in THF, 12.0 mmol) under nitrogen. The reaction mixture was stirred at 70° C. overnight and cooled to 0° C. Methanol (2 mL) was added followed by the addition of 1N HCl (2 mL). After refluxing for 30 min, the solution was diluted with water and extracted with EtOAc. The aqueous layer was basified with 1N NaOH and extracted with EtOAc twice. The combined organic layers were washed with brine and dried over Mg2SO4. After removal of solvent, the residue was purified by column chromatography (0-10% MeOH—CH2Cl2) to give (2-tert-butyl-5-nitrophenyl)methanamine (268 mg, 43%). 1H NMR (400 MHz, DMSO-d6) δ 8.54 (d, J=2.7 Hz, 1H), 7.99 (dd, J=8.8, 2.8 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 4.03 (s, 2H), 2.00 (t, J=2.1 Hz, 2H), 1.40 (s, 9H); HPLC ret. time 2.05 min, 10-100% CH3CN, 5 min gradient; ESI-MS 209.3 m/z (MH+).

Workup

temperaturecooled to 0° C
temperatureAfter refluxing for 30 min
extractionextracted with EtOAc
extractionextracted with EtOAc twice
washThe combined organic layers were washed with brine
dry with materialdried over Mg2SO4
customAfter removal of solvent
customthe residue was purified by column chromatography (0-10% MeOH—CH2Cl2)

Sources & evidence

ORD record: ord-6d031acdc8864cb6bbc5d3a66af0d73e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802700B2

Reaction notes

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