4-Fluoro-3-methoxybenzonitrile → 4-Fluoro-3-methoxybenzylamine

HRID 452290Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[C:12]#[N:13]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:12][NH2:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A flame dried 50 mL round bottom flask was charged with lithium aluminum hydride (0.63 g, 16.6 mmol) and to this was added tetrahydrofuran (25 mL). The solution was cooled to 0° C. and 3-methoxy-4-fluorobenzonitrile (1.0 g, 6.62 mmol) was added in one portion. The ice bath was removed after an hour and the resulting mixture was stirred for 16 h after which it was cooled to 0° C. and quenched by adding 0.63 mL water, 0.63 mL 15% NaOH and 1.89 mL water drop-wise and in succession. The mixture was stirred for 20 min and filtered. The filtrate was concentrated in vacuo to obtain 890 mg (86%) of the title compound as an oil. NMR indicated no further purification was required. NMR (300 MHz, DMSO-d6): δ 7.1 (m, 2H), 6.85 (m, 1H), 3.84 (s, 3H), 3.7 (s, 2H). 13C NMR (75 MHz, DMSO-d6): δ 150.0 (d, J=240 Hz), 146.6 (d, J=10.5 Hz), 141.1 (d, J=3.75 Hz), 118.75 (d, J=6.75 Hz), 115.1 (d, J=18 Hz), 112.5, 55.75, 45.2. HRMS: Calc'd for C8H10FNO (M+H): 156.0819; Found: 156.0818.

Workup

customA flame dried 50 mL round bottom flask
customThe ice bath was removed after an hour
temperaturewas cooled to 0° C.
customquenched
additionby adding 0.63 mL water, 0.63 mL 15% NaOH and 1.89 mL water
stirringThe mixture was stirred for 20 min
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-264e8162693845acb1fcedecb8667953
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08491868B2

Reaction notes

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