3-Methylbenzoyl chloride → HCID 11156487, compound

HRID 1064353Notes

Reaction equation

[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>N1C=CC=CC=1>[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([N:1]([C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([CH3:22])[CH:24]=1)[C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 5 g of 2-amino-3-cyano-4-benzylaminoquinoline in 30 ml of pyridine 6 ml of 3-methylbenzoyl chloride are dropped, under stirring at 0° C. The reaction mixture is stirred at 80° C. for 8 hour, then it is poured onto 150 ml of ice-water. The precipitate is filtered off, washed twice with 40 ml of water. The resulting white crystalline material is recrystallized from 200 ml of ethanol to give 9.2 g of the title compound, mp.: 234° C.

Workup

stirringThe reaction mixture is stirred at 80° C. for 8 hour
filtrationThe precipitate is filtered off
washwashed twice with 40 ml of water
customThe resulting white crystalline material is recrystallized from 200 ml of ethanol

Sources & evidence

ORD record: ord-7067f38f0aae444aa9bfe75d70071d65
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969723B2

Reaction notes

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