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6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline → N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

HRID 35229
Notes
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Reaction equation

HRID 35229 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:20]=[C:21]([CH2:25][C:26](O)=[O:27])[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[N+:16]([C:19]1[CH:20]=[C:21]([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:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 103026,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineHCID 10868DicyclohexylcarbodiimideHCID 158763-Nitrophenylacetic acid

Product 1

HCID 14230297N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinolineYield 64%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (20.0 g, 0.096 m) in methylene chloride (300 ml) under nitrogen at ambient temperature was added m-nitrophenylacetic acid (17.5 g, 0.096 m) and then portionwise dicyclohexylcarbodiimide (20.7 g, 0.1 m) and the mixture stirred for 3 hours. The precipitated solid was removed by filtration and the filtrate evaporated to an oily residue. This was treated with 100 ml methanol and 50 ml ether and the solid precipitate collected by filtration and washed with methanol and dried to give N-(3-nitrophenylacetyl)- 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as a yellow solid, 22.0 g (64% yield), m.p. 120°-121°.

Workup

  1. customThe precipitated solid was removed by filtration
  2. customthe filtrate evaporated to an oily residue
  3. additionThis was treated with 100 ml methanol and 50 ml ether
  4. filtrationthe solid precipitate collected by filtration
  5. washwashed with methanol
  6. customdried

Sources & evidence

ORD record
ord-bf0a2d4d017a45a3a5409ec7ef446b4b
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766131

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes