Acetic Acid → 7-Methoxy-1-naphthaleneethanamine

HRID 1511164Notes

Reaction equation

HRID 1511164 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.[BH4-].[Na+].C(O)(=O)C>CC(O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH2:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 44633448N-[2-(7-methoxy-1-naphthyl)ethyl]phthalimide

Product 1

HCID 110526677-Methoxy-1-naphthaleneethanamine

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

In a reactor, 1 g of the compound obtained in Step C and 5 eq. of NaBH4 are introduced into a 2-propanol/water 6/1 mixture, and the mixture is stirred at ambient temperature. Acetic acid (0.2 eq.) is then added and the reaction mixture is heated at 80° C. for 8 hours. After evaporating off the solvents and co-evaporation of water with toluene, the crude residue obtained is used directly in the acetylation reaction without further purification.

Workup

  1. temperaturethe reaction mixture is heated at 80° C. for 8 hours
  2. customAfter evaporating off the solvents and co-evaporation of water with toluene

Sources & evidence

ORD record
ord-35720e78bc4f40a58eb0b5a14acffd80
Source dataset
uspto-grants-2012_07
Patent number
US08212077B2

Reaction notes

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