반응 #816416

반응 방정식

13

N-acetyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

hydrazine hydrate

→

compound 14

수율 86.8%

N-acetyl-7-amino-1,2,3,4-tetrahydroisoquinoline

수율 86.8%

용매

methanol

반응 조건

후처리

1. 1
   온도under refluxing for 20 minutes
2. 2
   온도the mixture is refluxed for an additional 4 h
3. 3
   온도cooled
4. 4
   여과filtered
5. 5
   세척the residue washed with methanol
6. 6
   농축The filtrate is concentrated in vacuo
7. 7
   기타the residue recrystallized from EtOAc

실험 절차

A mixture of 13 (5.1 g, 23 mmol), activated carbon (4.2 g), ferric chloride hexahydrate (2.1 g, 7.6 mmol) and methanol (140 ml) is stirred under refluxing for 20 minutes. To the boiling mixture is added hydrazine hydrate (8.5 g, 265 mmol) dropwise, and the mixture is refluxed for an additional 4 h, cooled and filtered and the residue washed with methanol. The filtrate is concentrated in vacuo and the residue recrystallized from EtOAc to give compound 14 (3.8 g, 85% yield). 1H NMR [300 MHz, (CD3)2SO], a 3:2 mixture of amide conformers doubling most signals, δ 6.80 (1H, d, H-5), 6.40 (1H, d, H-6), 6.33 (1H, s, H-7), 4.89 (2H, br s, NH2), 4.46 (0.8H, s, ArCH2N), 4.41 (1.2H, s, ArCH2N), 3.57 (2H, t, ArCH2CH2N), 2.66 (1.2H, t, ArCH2CH2N), 2.55 (0.8H, t, ArCH2CH2N), 2.06 (1.2H, s, COCH3), 2.05 (1.8H, s COCH3).

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