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

HRID 35239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35239
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8a7abec084394b899e7192463b15817c
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766131

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