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

HRID 1451655
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HRID 1451655 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3fc329dc8814a0791f2b399213a34b6
출처 데이터셋
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05604237

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