Acetic Acid → HCID 86592229, compound

HRID 1530892Notes

Reaction equation

HRID 1530892 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([NH2:16])[C:13]2[C:8](=[CH:9][C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[CH:12]=2)[N:7]1[C:21]([O:23][CH:24]([CH2:26][CH3:27])[CH3:25])=[O:22])=[O:5])[CH3:2].C(O)(=O)C.[F:32][C:33]([F:47])([F:46])[C:34]1[CH:35]=[C:36]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH:37]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([NH:16][CH2:37][C:36]2[CH:39]=[C:40]([C:42]([F:44])([F:45])[F:43])[CH:41]=[C:34]([C:33]([F:32])([F:46])[F:47])[CH:35]=2)[C:13]2[C:8](=[CH:9][C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[CH:12]=2)[N:7]1[C:21]([O:23][CH:24]([CH2:26][CH3:27])[CH3:25])=[O:22])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86592227HCID 86592227, compound

Product 1

HCID 86592229HCID 86592229, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-amino-6,7-dimethoxy-3,4-dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester (Example 3) (500 mg, 1.30 mmol) in anhydrous dichloroethane (30 mL) was added acetic acid (79 mg, 1.30 mmol), followed by 3,5-bis(trifluoromethyl)benzaldehyde (318 mg, 1.30 mmol) and sodium triacetoxyborohydride (418 mg, 1.97 mmol). The reaction was stirred at room temperature for 30 min. The reaction mixture was then diluted with chloroform and washed with 1N NaOH. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the crude title compound (approximately 500 mg) which was used directly in Example 5.

Workup

  1. washwashed with 1N NaOH
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92e26c33ec724ac0b58f15dec91331c7
Source dataset
uspto-grants-2001_03
Patent number
US06197786B1

Reaction notes

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