Sodium Hydroxide → 2-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1153973Notes

Reaction equation

HRID 1153973 reaction equation
[OH-:1].[Na+].BrC(Br)[C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)=[O:6]>O>[C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)([OH:6])=[O:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131049236-(Dibromoacetyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 54.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 250 ml of water, 26 g sodium hydroxide was dissolved, then at a temperature of 90°-100° C. and under stirring condition, 35 g of 6-dibromoacetyl-3,4-dihydrocarbostyril was added thereinto and reacted for 3 hours. After the reaction was completed, the reaction mixture was cooled and insoluble matters formed in the mixture were removed by filtration. The mother liquor was acidified with concentrated hydrochloric acid and the crystals precipitated were collected by filtration and washed with water. The crystals thus obtained were recrystallized from ethanol twice to obtain 10.5 g of 6-carboxy-3,4-dihydrocarbostyril in the form of light yellow amorphous crystals. Melting point: 324.5°-327° C. (decomposed)

Workup

  1. additionwas added
  2. customreacted for 3 hours
  3. temperaturethe reaction mixture was cooled
  4. custominsoluble matters formed in the mixture
  5. customwere removed by filtration
  6. customthe crystals precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customThe crystals thus obtained
  10. customwere recrystallized from ethanol twice

Sources & evidence

ORD record
ord-502251ee189c4618a83dc21372b1b16a
Source dataset
uspto-grants-1984_12
Patent number
US04487772

Reaction notes

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