Water → 2-[1,1'-Biphenyl]-4-yl-3-(ethylamino)-6-fluoro-4-quinolinecarboxylic acid

HRID 1073255Notes

Reaction equation

HRID 1073255 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.[BH4-].[Na+].O>O1CCCC1>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:16]([NH:17][CH2:18][CH3:22])=[C:15]([C:20]([OH:21])=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([F:23])[CH:13]=3)[N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 150859865-[1,1'-Biphenyl]-4-yl-9-fluoro-3-methyl-1H-[1,3]oxazino[4,5-c]quinolin-1-one

Product 1

HCID 150859482-[1,1'-Biphenyl]-4-yl-3-(ethylamino)-6-fluoro-4-quinolinecarboxylic acidYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.0 g of 5-[1,1'-biphenyl]-4-yl-9-fluoro-3-methyl-1H-[1,3]oxazino[4,5-c] quinoline-1-one in 200 ml of tetrahydrofuran at 0° C. was added 0.91 g of sodium borohydride. The solution was stirred at 0° C. for 1 hour, then allowed to warm to 20° C. and stirred for 12 hours. A 50 ml portion of water was added and the foaming solution stirred for 10 minutes. The volatiles were removed in vacuo, then 40 ml of 0.5N sodium hydroxide was added and the solution extracted with two 100 ml portions of dichloromethane. The extracts were combined, extracted with 100 ml of water containing 5 ml of 1N sodium hydroxide and the aqueous layer from this extraction extracted with 100 ml of dichloromethane. The aqueous layers were combined, filtered through celite and acidified to pH 4 with 3 % aqueous hydrochloric acid. The resulting solid was collected, washed with water and dried, giving 2.8 g of the desired product as a yellow solid, mp 180°-182° C. (dec.)

Workup

  1. temperatureto warm to 20° C.
  2. stirringstirred for 12 hours
  3. stirringthe foaming solution stirred for 10 minutes
  4. customThe volatiles were removed in vacuo
  5. addition40 ml of 0.5N sodium hydroxide was added
  6. extractionthe solution extracted with two 100 ml portions of dichloromethane
  7. extractionextracted with 100 ml of water containing 5 ml of 1N sodium hydroxide
  8. extractionthe aqueous layer from this extraction
  9. extractionextracted with 100 ml of dichloromethane
  10. filtrationfiltered through celite
  11. customThe resulting solid was collected
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-011758a0b22f449e9d002ad487cf5554
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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