Hydrogen Bromide → HCID 21260383, compound

HRID 634639Notes

Reaction equation

HRID 634639 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2(O)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[NH:11][C:10](=[O:22])[CH:9]2[CH2:23][C:24]([O:26]C)=[O:25])[CH:7]=1.Br>C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[NH:11][C:10](=[O:22])[C:9]=2[CH2:23][C:24]([OH:26])=[O:25])[CH:7]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 10917239HCID 10917239, compound

Product 1

HCID 21260383HCID 21260383, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A stirred suspension of crude 4-(5-chloro-2-methoxyphenyl)-4-hydroxy-1,2,3,4-tetrahydro-2-oxo-6-(trifluoromethyl)-3-quinolineacetic acid, methyl ester prepared in Step B (2 g, 4.5 mmol) in toluene (25 mL) was treated with a solution of 35% HBr in acetic acid (5 mL). The resultant mixture was heated at 85° C. overnight. The reaction mixture was evaporated to dryness and the residue was partitioned between water and EtOAc. The EtOAc extract was washed with brine and dried (MgSO4) and then evaporated to afford the title compound (1.45 g, 78%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was partitioned between water and EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a8290662f6fc4b54a3d1f350a22f953f
Source dataset
uspto-grants-2001_02
Patent number
US06184231B2

Reaction notes

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