Aluminium lithium hydride → 2-(3-Fluoro-4-methoxyphenyl)ethanamine

HRID 216095Notes

Reaction equation

HRID 216095 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N+:10]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 534146392-Fluoro-1-methoxy-4-(2-nitro-vinyl)benzene2×

Product 1

HCID 4263002-(3-Fluoro-4-methoxyphenyl)ethanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2-fluoro-1-methoxy-4-(2-nitro-vinyl)benzene (1.5 g, Intermediate (2)] in THF (50 mL) is treated dropwise with a solution of lithium aluminum hydride in ether (23 mL, 1M). The mixture is heated at 40° C. for 3 hours, cooled to room temperature, diluted with ether and quenched with Na2SO4.10H2O (104 g). After standing at room temperature overnight the reaction mixture is filtered and the filtrate is evaporated. The residue is subjected to chromatography on silica gel eluting with EtOAc to give 2-(3-fluoro-4-methoxy-phenyl)-ethylamine [0.81 g, Intermediate (3)] as an oil. MS: 170 (M+H); 1H NMR (CDCl3): 6.9-7 (3H, m); 3.85 (3H, s); 2.95 (2H, t); 2.7 (2H, t).

Workup

  1. temperaturecooled to room temperature
  2. customquenched with Na2SO4.10H2O (104 g)
  3. filtrationthe reaction mixture is filtered
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-79ad4e3602a341269019ad6f28a77b98
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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