HCID 18621449, compound → HCID 54549658, compound

HRID 324561Notes

Reaction equation

HRID 324561 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[CH:4][C:3]=1[N+:22]([O-])=O>CCO>[NH2:22][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:2]=1[NH2:1])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1

Participants

3

Reactant 1

HCID 18621449HCID 18621449, compound

Product 1

HCID 54549658HCID 54549658, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

From a mixture of N-[3-(4-amino-3-nitrophenoxy)propyl]isoquinoline (250 mg, 0.76 mmol) and stannous dihydrate (860 mg, 3.8 mmol) in EtOH (50 mL) was obtained 220 mg (97%) of N-[(3,4-diaminophenoxy)propyl]-1,2,3,4-tetrahydroisoquinoline as a yellow viscous oil. 1H NMR (CDCl3): 2.00-2.08 (m, 2H), 2.686 (t, 2H, J=7), 2.761 (t, 2H, J=5.5), 2.916 (t, 2H, J=5.5), 3.063 (s, 2H), 3.496 (s, 2H), 3.650 (s, 2H), 3.995 (t, 2H, J=7), 6.267 (dd, 1H, J=8.5; 2.5), 6.340 (d, 1H, J=2.5), 6.670 (d, 1H, J=8.5), 7.01-7.12 (m, 4H).

Sources & evidence

ORD record
ord-d92110020be5495ebe40e648044ee5c7
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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