Acetic Acid → HCID 25116797, compound

HRID 408665Notes

Reaction equation

HRID 408665 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:23])[CH:8]=2)[N:3]=1.[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.[OH-].[Na+]>[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:23][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68725336HCID 68725336, compound

Product 1

HCID 25116797HCID 25116797, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Methyl-6-amino-4-(3-phenylpyrrolidin-1-yl)quinoline (0.08 g; see Example 45 below), 4-methoxybenzaldehyde (0.071 g), sodium triacetoxyborohydride (0.165 g) and acetic acid (0.05 mL) in 1,2-dichloroethane (5 mL) was refluxed for 4 hours. The reaction mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica, eluting with a mixture of dichloromethane, and methanol. The desired fractions were concentrated and the sample evaporated to dryness. Trituration from ether gave the title compound as a white powder (0.01 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of dichloromethane, and methanol
  8. concentrationThe desired fractions were concentrated
  9. customthe sample evaporated to dryness

Sources & evidence

ORD record
ord-9befb4a5fe77449ebe686d4f9bb633ee
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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