Acetic Acid → HCID 68194140, compound

HRID 1520180Notes

Reaction equation

HRID 1520180 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:30]([O:32]C)=[O:31])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].CC(O)=O>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:30]([OH:32])=[O:31])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 68194005HCID 68194005, compound

Product 1

HCID 68194140HCID 68194140, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(7-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (88 mg, 0.20 mmol) in methanol (30 ml) was added sodium hydroxide (32 mg, 0.80 mmol) and water (2 ml). The reaction was stirred for 2 days at room temperature. The resulting solution was diluted with water (15 ml), adjusted to pH 5 with AcOH, extracted with ethyl acetate (2×20 ml) and the organic layers were combined and concentrated in vacuo to afford 2-(4-fluorophenyl)-3-(7-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (59 mg, 69%).

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ed7a4011a4c4a5ab7605d6539e12d19
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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