Potassium Hydroxide → 2-(4'-Chloro-4-methoxy-biphen-2-yl)-quinoline-6-carboxylic acid

HRID 1788552Notes

Reaction equation

HRID 1788552 reaction equation
[CH3:1][O:2]C(=O)C1C=CC(N)=C(C=O)C=1.[OH-].[K+].[Cl:16][C:17]1[CH:48]=[CH:47][C:20]([C:21]2[C:26]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[C:32]([C:37]([OH:39])=[O:38])[CH:33]=4)[N:28]=3)=[CH:25][C:24](C(N3CCCC3)=O)=[CH:23][CH:22]=2)=[CH:19][CH:18]=1>CCO>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]2[C:26]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[C:32]([C:37]([OH:39])=[O:38])[CH:33]=4)[N:28]=3)=[CH:25][C:24]([O:2][CH3:1])=[CH:23][CH:22]=2)=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 46911801Methyl 4-amino-3-formylbenzoateHCID 576029872-[4'-Chloro-4-(pyrrolidine-1-carbonyl)-biphen-2-yl]-quinoline-6-carboxylic acid

Product 1

HCID 860273132-(4'-Chloro-4-methoxy-biphen-2-yl)-quinoline-6-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 7 (3.06 g. 11.72 mmol) was reacted with compound 525a (2.1 g, 11.72 mmol) and KOH (2.32 g, 35.16 mmol) in EtOH (150 mL) according to the procedure in the preparation of Compound 259e. Purification by chromatography using CHCl3-MeOH (7:1) as the eluent gave the title intermediate (3.1 g, 91%). MS: 388.07 (M+H+).

Workup

  1. customPurification by chromatography

Sources & evidence

ORD record
ord-8cc70d6dc4db4e4f9f8dc74e63e90d69
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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