(4-Nitrophenyl)acetic acid → N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

HRID 35224

Reaction equation

HRID 35224 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH3:15])[NH:8][CH2:7][CH2:6]2.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](O)=[O:27])=[CH:21][CH:20]=1)([O-:18])=[O:17].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][C:26]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]2[CH3:15])=[O:27])=[CH:23][CH:24]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 103026,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 14230283N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methyl-isoquinoline (35.2 g, 0.17 m) in methylene chloride (50 ml) under nitrogen at ambient temperature was added p-nitrophenylacetic acid (31.4 g, 0.17 m) and then portionwise dicyclohexylcarbodiimide (37.0 g, 0.18 m) and the mixture stirred for 3 hr. The precipitated solid was removed by filtration and the filtrate evaporated to an oily residue. The residue was treated with 500 ml methanol and the solid precipitate collected by filtration to give, after drying, N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as a yellow solid, 66.0 g (100+% yield). The product contains a small amount of dicyclohexylurea.

Workup

  1. customThe precipitated solid was removed by filtration
  2. customthe filtrate evaporated to an oily residue
  3. additionThe residue was treated with 500 ml methanol
  4. filtrationthe solid precipitate collected by filtration
  5. customto give
  6. customafter drying

Sources & evidence

ORD record
ord-5709e522cf2545aba9ebb7dcb7f06f67
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Linked notes

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