Isatin → 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one

Reaction equation

N1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[NH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16]>>[CH:17]1[CH:18]=[CH:19][CH:20]=[C:13]2[C:14]=1[C:15]1[NH:16][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]=1[C:2](=[O:3])[NH:12]2

Participants

Reactant 2

HCID 7054Isatin

HCID 1780962-(Aminomethyl)aniline

Product 1

HCID 27848815,11-dihydro-6H-indolo[3,2-c]quinolin-6-one

Procedure

Specifically, as shown in Scheme 1, reaction of isatin (1) and 2-aminobenzylamine (2) gives 5,11-dihydro-indolo[3,2-c]quinolin-6-one (3), which may be treated with POCl3 to yield 6-chloro-11H-indolo[3,2-c]quinoline (4), which may be further reacted with either an amine of formula R—NH2 or a diamine of formula H2N—R—NH2 to give a corresponding compound of either formula (IA) or formula (IB).

Sources & evidence

ORD record: ord-b7934138da18444db9d3a05bc2d68786
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273760B2

Reaction notes

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