Phenylacetic Acid → HCID 178524026, compound

HRID 1170877Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[OH:3][C:2]1[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:18]([C:19]([OH:21])=[O:20])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:1]=1

Participants

Reactant 2

HCID 999Phenylacetic Acid

HCID 7054Isatin

Product 1

HCID 178524026HCID 178524026, compound

Procedure

As shown in Scheme 1, reaction of isatin (1) and phenylacetic acid (2) gives 2-hydroxy-3-phenylquinoline-4-carboxylic acid (3), which may be treated with POCl3 to yield 6-chloro-11H-indeno[1,2-c]quinolin-11-one (4). Reaction of a compound 4 with a compound of formula R9AH, such as piperazine, yields a compound 5, such as 6-(piperazin-1-yl)-11H-indeno[1,2-c]quinolin-11-one (compd. 5x in Synthesis Ex. 9, infra), which may be reacted either with NH2OH, optionally followed by alkylation with an alkyl halide of formula R10X, or with NH2OR10 directly, to give a corresponding compound of formula (I).

Sources & evidence

ORD record: ord-2399939f1bff45b9b9c3d4d30b6d5d61
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829567B2

Reaction notes

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