Sodium Hydroxide → Brequinar sodium

HRID 1086826Notes

Reaction equation

HRID 1086826 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]([CH3:24])=[C:22]([C:25]([OH:27])=[O:26])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:28])[CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1.[OH-].[Na+:30]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]([CH3:24])=[C:22]([C:25]([O-:27])=[O:26])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:28])[CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1.[Na+:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57030Brequinar

Product 1

HCID 23663964Brequinar sodiumYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 28 (37.5 g, 0.10 mole) was suspended in 1,000 ml of ethanol and treated with 1N NaOH (100 ml, 0.10 mole). The mixture was warmed and stirred until clear; the ethanol and water were evaporated at reduced pressure to give 39.6 g of the white solid sodium 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methylquinoline-4-carboxylate, m.p. >360°.

Workup

  1. temperatureThe mixture was warmed
  2. customthe ethanol and water were evaporated at reduced pressure

Sources & evidence

ORD record
ord-05faa2a711d3449593541c99e5ed9f11
Source dataset
uspto-grants-1991_07
Patent number
US05032597

Reaction notes

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