Carbon Dioxide → HCID 12802778, compound

HRID 1390289Notes

Reaction equation

HRID 1390289 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[C:9]([CH3:17])=[CH:8][C:7]1=[O:18].C([Li])CCC.[C:28](=[O:30])=[O:29].Cl>CCCCCC.O1CCCC1.O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[C:9]([CH2:17][C:28]([OH:30])=[O:29])=[CH:8][C:7]1=[O:18]

Participants

9

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 203756121-[(3,4-Dichlorophenyl)methyl]-7-fluoro-4-methylquinolin-2(1H)-oneHCID 178418339Butyllithium

Product 1

HCID 12802778HCID 12802778, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Procedure

1-(3,4-Dichlorobenzyl)-1,2-dihydro-7-fluoro-4-methyl-2-oxoquinoline (7g.) was added portionwise to a solution of n-butyl-lithium (9.8 ml. of a 2.32 N-solution in hexane) and triethylamine (1.15 g.) in dry tetrahydrofuran (150 ml.) maintained at -40° C. The mixture was stirred at -30° C. to -40° C. for one hour under an atmosphere of dry argon, and then added to a saturated solution of dry carbon dioxide in dry tetrahydrofuran (200 ml.). The mixture was stirred at -30° C. for 2 hours and then allowed to reach ambient temperature overnight. Water (400 ml.) was added and the concentrated hydrochloric acid to bring the pH of the mixture to 3-4. The crude acid was filtered off and recrystallised from methanol to give 1-(3,4-dichlorobenzyl)-1,2-dihydro-7-fluoro-2-oxoquinol-4-ylacetic acid, m.p. 205°-207° C. (dec.), in 66% yield.

Workup

  1. stirringThe mixture was stirred at -30° C. for 2 hours
  2. waitto reach ambient temperature overnight
  3. filtrationThe crude acid was filtered off
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-66907e5983fb491ab78ffaa141b9cc56
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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