Acetic Acid → HCID 58415922, compound

HRID 1943034Notes

Reaction equation

HRID 1943034 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH:12]=O)[C:3]1=[O:14].C([O-])(=O)C.[Na+].[Cl-].[Cl-].[NH3+:22][CH2:23][CH:24]([NH+:31]1[CH2:36][CH2:35][C:34]([F:38])([F:37])[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:38][C:34]1([F:37])[CH2:33][CH2:32][N:31]([CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][NH:22][CH2:12][C:4]2[C:3](=[O:14])[N:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:36][CH2:35]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86657267HCID 86657267, compound

Product 1

HCID 58415922HCID 58415922, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (35 mg, 0.187 mmol), sodium acetate (19.94 mg, 0.243 mmol), and 1-(2-ammonio-1-phenylethyl)-4,4-difluoropiperidinium dichloride (51.7 mg, 0.187 mmol) were combined in 1,2-dichloroethane (2 ml). Acetic acid (0.021 ml, 0.374 mmol) and sodium triacetoxyborohydride (119 mg, 0.561 mmol) were added and the reaction stirred for 1 hour. The reaction mixture was partitioned between CH2Cl2 and satd. bicarb, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The material was carried on without further purification.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and satd
  2. extractionbicarb, the aqueous portion extracted 3×CH2Cl2
  3. dry with materialthe organic portion dried (Na2SO4)
  4. concentrationthen concentrated in vacuo
  5. customThe material was carried on without further purification

Sources & evidence

ORD record
ord-04d49e74880c4ab2a7f447ed22dcd4c2
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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