(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine → 6-(benzyloxy)-N4-methylquinoline-3,4-diamine

HRID 2383130Notes

Reaction equation

HRID 2383130 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-])=O)=[C:12]2[NH:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C2C(C(NCCOC3C=CC=CC=3)=C([N+]([O-])=O)C=N2)=CC=1)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:22][CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 67050949(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amineHCID 67051077N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine

Product 1

HCID 670510076-(benzyloxy)-N4-methylquinoline-3,4-diamineYield 77.2%

Procedure

The general method described in Part B of Example 46 was followed using N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine (11.36 g, 36.7 mmol) in lieu of (7-benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine. 6-Benzyloxy-N4-methylquinoline-3,4-diamine (7.91 g) was obtained as a dark yellow oil and used without purification.

Sources & evidence

ORD record
ord-cabdc05c2ba7402ab8140e207b7189e6
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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