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

HRID 35239ノート

反応式

HRID 35239 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-8a7abec084394b899e7192463b15817c
出典データセット
uspto-grants-1988_08
特許番号
US04766131

反応ノート

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