N-bromobutanimide → 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

HRID 1853662Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[NH:9][C:8](=[O:14])[C:7]3[S:15][CH:16]=[CH:17][C:6]=3[C:5]=2[CH:4]=1.[Br:18]N1C(=O)CCC1=O>>[Br:18][C:4]1[C:5]2[C:6]3[CH:17]=[CH:16][S:15][C:7]=3[C:8](=[O:14])[NH:9][C:10]=2[C:11]([CH3:13])=[CH:12][C:3]=1[O:2][CH3:1]

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 674508408-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 674500069-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneYield 83%

Procedure

Following Step 4 from General Procedure A, 8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (6.4 g, 26 mmol) was reacted with N-bromosuccinimide (5.0 g, 26 mmol) to afford the desired product (7.0 g, 82%) as a brown solid: ESI MS m/z 329 [C12H7BrFNO2S+H]+.

Sources & evidence

ORD record: ord-d55d6652500e4a33b9ac82b843914eca
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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