Hydrochloric Acid → 3-Bromo-2-methylaminomethyl-phenylamine

HRID 459790Notes

Reaction equation

HRID 459790 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[C:15]([Br:16])=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:17])C)(C)(C)C.Cl.C([O-])(O)=O.[Na+].C(OCC)(=O)C>C(O)C>[Br:16][C:15]1[C:10]([CH2:9][NH:7][CH3:6])=[C:11]([NH2:17])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 58824133(2-Amino-6-bromo-benzyl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 184444723-Bromo-2-methylaminomethyl-phenylamineYield 765.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

(2-Amino-6-bromo-benzyl)-methyl-carbamic acid tert-butyl ester (371 mg) was dissolved in 50 ml ethanol. To this solution was added 2M ethanolic hydrochloride acid solution (10 ml). The reaction mixture was heated at 100° C. for 30 minutes, at which time the deprotection was completed. The solution was allowed to cool to room temperature and poured into the mixture of saturated NaHCO3 solution and ethyl acetate. The aqueous layer was extracted with EtOAc three times and the organic fractions were concentrated to give 3-bromo-2-methylaminomethyl-phenylamine as a brown oil (1.938 g, 76%). MS: (M+H)+217.1.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. concentrationthe organic fractions were concentrated

Sources & evidence

ORD record
ord-47f0bde3834a410da7b8f1065629cbe4
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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