Diethyl Ether → 2-(3-Fluoro-4-methoxyphenyl)ethanamine

HRID 2386461Notes

Reaction equation

HRID 2386461 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[F:12][C:13]1[CH:18]=[C:17]([CH:19]=[CH:20][N+:21]([O-])=O)[CH:16]=[CH:15][C:14]=1[O:24][CH3:25]>C(OCC)(=O)C>[F:12][C:13]1[CH:18]=[C:17]([CH2:19][CH2:20][NH2:21])[CH:16]=[CH:15][C:14]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 534146392-Fluoro-1-methoxy-4-(2-nitro-vinyl)benzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (200 mL of 1 M in diethyl ether) was placed in a 1 L round bottomed flask along with 300 mL of diethyl ether. Intermediate 81 was placed in the thimble of a soxhlet extractor atop this flask and the mixture refluxed for 24 hours. The mixture was cooled to 0° C. and 50 mL of ethyl acetate added dropwise. After stirring for 1 hour, the mixture was quenched with 100 mL of 1 N KHSO4. The Organic layer was separated washed with sat. NaHCO3, sat. NaCl, and dried over MgSO4. Removal of the solvent gave product. LC-MS showed the product had the expected M+H+ of 170. It was used in the next step without purification.

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. customthe mixture was quenched with 100 mL of 1 N KHSO4
  3. customThe Organic layer was separated
  4. washwashed with sat. NaHCO3, sat. NaCl
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent
  7. customgave product
  8. customIt was used in the next step without purification

Sources & evidence

ORD record
ord-41580f432f8f47d996d7cc9ab2f70b0f
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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