甲酸 → N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

HRID 35239笔记

反应方程式

HRID 35239 反应方程式
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH3:20])=[CH:4][CH:3]=1.[CH:23](O)=[O:24]>C1(C)C=CC=CC=1>[CH:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH3:20])=[CH:21][CH:22]=1)=[O:24]

参与物

4

反应物 2

HCID 284甲酸HCID 14230290N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

产物 1

HCID 14230294N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

实验过程

To a stirred solution of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (16.8 g, 0.057 m) in 800 ml toluene was added formic acid (25.0 g, 0.5 m). The reaction was brought to reflux, and water was collected by a Dean-Stark apparatus. After 1 hour, the reaction was poured into ice water (500 g) and basified to pH 11-12 with 10% NaOH. The toluene layer was separated, and the aqueous layer was extracted further with toluene (1×200 ml) and then with chloroform (2×200 ml). The organic extracts were combined, dried and concentrated to an oil. The oil was dissolved in 100 ml ether and a solid formed which was filtered off and dried to give N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6 -methoxy-1-methylisoquinoline, wt. 12.0 g (71%), m.p. 93°-96°.

后处理

  1. temperatureto reflux
  2. customwater was collected by a Dean-Stark apparatus
  3. additionthe reaction was poured into ice water (500 g)
  4. customThe toluene layer was separated
  5. extractionthe aqueous layer was extracted further with toluene (1×200 ml)
  6. customdried
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in 100 ml ether
  9. customa solid formed which
  10. filtrationwas filtered off
  11. customdried

来源与证据

ORD记录
ord-8a7abec084394b899e7192463b15817c
来源数据集
uspto-grants-1988_08
专利号
US04766131

反应笔记

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