Benzylamine → 2-Amino-3-cyano-4-benzylamino-6-nitroquinoline

HRID 1985698Notes

Reaction equation

[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=2)[N:3]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 7 g of 2-amino-3-cyano-4-chloro-6-nitroquinoline and 30 mL of benzylamine was stirred at 55° C. for 1.5 hours. The reaction mixture is poured onto 30 mL of water. The precipitated material is filtered off, washed with water to give 7 g of the title compound, m.p.: 280-283° C. LC-MS: MH+ 2320; Ret. time: 5.19 minutes.

Workup

filtrationThe precipitated material is filtered off
washwashed with water

Sources & evidence

ORD record: ord-f9aab62b52e5416897e453cb450a1f30
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547696B2

Reaction notes

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