Hydrochloric Acid → 3-(Acetylamino)-2-[1,1'-biphenyl]-4-yl-6-fluoro-4-quinolinecarboxylic acid

HRID 1073256Notes

Reaction equation

HRID 1073256 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[N:17]=[C:18]([CH3:22])[O:19][C:20](=[O:21])[C:15]=3[C:14]3[CH:13]=[C:12]([F:23])[CH:11]=[CH:10][C:9]=3[N:8]=2)=[CH:3][CH:2]=1.[OH2:30].[OH-].[Na+].Cl>O1CCCC1>[C:18]([NH:17][C:16]1[C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:2][CH:3]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:20]([OH:30])=[O:21])=[CH:13][C:12]([F:23])=[CH:11][CH:10]=2)(=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 150859865-[1,1'-Biphenyl]-4-yl-9-fluoro-3-methyl-1H-[1,3]oxazino[4,5-c]quinolin-1-one

Product 1

HCID 150859503-(Acetylamino)-2-[1,1'-biphenyl]-4-yl-6-fluoro-4-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.8 g portion of 5-[1,1'-biphenyl]-4-yl-9-fluoro-3-methyl-1H-[1,3]oxazino[4,5-c]quinolin-1-one was dissolved in 50 ml of tetrahydrofuran. To this was added 10 ml of water containing 0.94 ml of 1N sodium hydroxide. This mixture was stirred for 4 hours, then poured into 500 ml of water and acidified to pH 4 with 3% aqueous hydrochloric acid. The resulting solid was collected, washed with water and dried at 110° C. in vacuo, giving 1.6 g of the desired product as a white solid mp 256°-259° C.

Workup

  1. customThe resulting solid was collected
  2. washwashed with water
  3. customdried at 110° C. in vacuo

Sources & evidence

ORD record
ord-1533af8ed27541ec8df49d3173781887
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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