Acetic Acid → HCID 86755987, compound

HRID 370045Notes

Reaction equation

HRID 370045 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C@H:9]([NH2:19])[CH2:8][C@@H:7]1[CH3:20])=[O:5])[CH3:2].[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH:26]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C@H:9]([NH:19][CH2:26][C:25]2[CH:28]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:30]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=2)[CH2:8][C@@H:7]1[CH3:20])=[O:5])[CH3:2]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69833805HCID 69833805, compound

Product 1

HCID 86755987HCID 86755987, compoundYield 60.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of cis-4-amino-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (4.49 g, 16.0 mmol) in 1,2-dichloroethane (100 mL) was added 3,5-bis(trifluoromethyl)benzaldehyde (2.6 mL, 16.0 mmol), followed by acetic acid (0.9 mL, 16.0 mmol). After 45 min, sodium triacetoxyborohydride (5.1 g, 24.0 mmol) was added, and the reaction was stirred at room temperature overnight. Water (75 mL) and ethyl acetate (75 mL) were added to the mixture which was then made basic to pH 10 with solid potassium carbonate. The mixture was then extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 8.17 g of crude product. Purification by silica gel chromatography using 0-30% ethyl acetate/hexanes as eluent afforded 4.90 g of the title compound (60%).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (2×100 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 8.17 g of crude product
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-a773f0f7ead44d24af75b01f241e01d4
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

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