Water → 1-Carbomethoxy-2-benzylamino-3,4-dihydronaphthalene

HRID 1350192Notes

Reaction equation

HRID 1350192 reaction equation
[C:1]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=O)([O:3][CH3:4])=[O:2].C(O)(=O)C(C)C.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>C1(C)C=CC=CC=1>[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]=1[NH:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6590Isobutyric AcidHCID 7504BenzylamineHCID 5991311-Naphthalenecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, methyl ester

Product 1

HCID 210946731-Carbomethoxy-2-benzylamino-3,4-dihydronaphthaleneYield 102.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-carbomethoxy-2-oxo-1,2,3,4-tetrahydronaphthalene (10.2 g) and isobutyric acid (4.84 g) in toluene (150 mL) stirring at room temperature under argon, was added benzylamine (5.35 g). The resulting mixture was heated to reflux for 2 h with water removal using a Dean-Stark trap. The solvent was then evaporated under vacuum to provide the title compound (15 g) as a yellow gum.

Workup

  1. temperatureThe resulting mixture was heated
  2. customThe solvent was then evaporated under vacuum

Sources & evidence

ORD record
ord-e1562b7a1b0342efa5869dca9cb48120
Source dataset
uspto-grants-2007_05
Patent number
US07214704B2

Reaction notes

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