Hydrochloric Acid → 2-(3-Bromo-5-methoxyphenyl)ethan-1-amine

HRID 2069079Notes

Reaction equation

HRID 2069079 reaction equation
C1COCC1.[Br:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]#[N:17])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.Cl.[OH-].[Na+]>C(OCC)(=O)C.CO>[Br:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][NH2:17])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 212429652-(3-Bromo-5-methoxyphenyl)acetonitrile

Product 1

HCID 106094762-(3-Bromo-5-methoxyphenyl)ethan-1-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A borane-tetrahydrofuran complex (1 M, 73.6 mL) was added to a THF (36.8 mL) solution of Intermediate 3 at room temperature and the resulting mixture was stirred to reflux at 80° C. for 2 hours. Methanol (26 mL) and 1 N hydrochloric acid (26 mL) were added to the reaction mixture solution and the resulting mixture was stirred at room temperature for 1 hour. The resulting mixture was neutralized with 1 N aqueous sodium hydroxide solution followed by the addition of ethyl acetate (100 mL) to extract the reaction mixture, the organic layer was dried, and then the solvent was evaporated under reduced pressure to give the title compound (8.76 g).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. extractionto extract the reaction mixture
  3. customthe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-311631ca28cd4032830eee9f6352f8bd
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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