Dicyclohexylcarbodiimide → 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[(4-methoxy-3-nitrophenyl)acetyl]isoquinoline

HRID 1451655Notes

Reaction equation

HRID 1451655 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].ON1C2C=CC=CC=2N=N1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[CH2:34][NH:33][CH2:32][CH2:31]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[CH2:34][N:33]([C:10](=[O:12])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=1)[CH2:32][CH2:31]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 757711-HydroxybenzotriazoleHCID 43305212-(4-Methoxy-3-nitrophenyl)acetic acid

Product 1

HCID 199744821,2,3,4-Tetrahydro-6,7-dimethoxy-2-[(4-methoxy-3-nitrophenyl)acetyl]isoquinolineYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-methoxy-3-nitrophenylacetic acid (1.2 g) and 1-hydroxybenzotriazole (0.95 g) in DMF (30 ml) was stirred at room temperature for 10 min. 1,2,3,4-Tetrahydro-6,7-dimethoxy-isoquinoline (1.1 g) in DMF (20 ml) was then added, followed by dicyclohexylcarbodiimide (1.2 g) and the mixture was stirred at room temperature for 6 h and then filtered. The filtrate was concentrated in vacuo, treated with dilute sodium hydroxyde and extracted with ethyl acetate. The dried organic extract was evaporated to give the title compound (1.6 g) as an oil which crystallised from ethanol as a white solid, MP 175°. IR: Freq CO: 1650 cm-1.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with dilute sodium hydroxyde
  5. extractionextracted with ethyl acetate
  6. extractionThe dried organic extract
  7. customwas evaporated

Sources & evidence

ORD record
ord-a3fc329dc8814a0791f2b399213a34b6
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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