2-Methyl-1-naphthylamine → HCID 13117216, compound

HRID 1589160Notes

Reaction equation

HRID 1589160 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].C(=O)(O)[O-].[Na+].Br[CH:19]([CH2:24][CH3:25])[C:20]([O:22][CH3:23])=[O:21]>>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[NH:1][CH:19]([CH2:24][CH3:25])[C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 3

HCID 167332-Methyl-1-naphthylamineHCID 95577Butanoic acid, 2-bromo-, methyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 13117216HCID 13117216, compoundYield 86.3%

Procedure

144.2 g (0.92 mole) of 1-amino-2-methylnaphthalene are stirred with 90.2 g (1.08 moles) of sodium bicarbonate and 507 g (2.8 moles) of methyl 2-bromobutyrate at from 120° to 125° C. for 18 hours. The mixture is cooled, and thereafter the precipitate is filtered off under suction, the filtrate is concentrated under reduced pressure, and the residue is distilled under reduced pressure. 204.3 g (79.5% of theory) of methyl 2-(2-methylnaphth-1-ylamino)-butyrate are obtained as a colorless oil. Boiling point: 148°-150° C./0.25 mbar; nD25 =1.5779.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe precipitate is filtered off under suction
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-44e22f9430964bd28edd707b7051e2f2
Source dataset
uspto-grants-1986_02
Patent number
US04568684

Reaction notes

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