Pyrrolidine → HCID 23022384, compound

HRID 351346Notes

Reaction equation

HRID 351346 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([CH:13]=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:12][C:11]1[C:2]([NH2:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][C:7]([CH2:13][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:6]2

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 230223367-Amino-8-methylquinoline-3-carbaldehyde

Product 1

HCID 23022384HCID 23022384, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 7-amino-8-methyl-3-quinolinecarboaldehyde (21.00 g, 112.8 mmol) obtained in Reference Example 66 in dichloroethane (210 ml) were added pyrrolidine (28.28 ml, 145.0 mmol) and triacetoxy sodium borohydride (35.84 g, 169.2 mmol), and the mixture was stirred at room temperature for 4.5 hrs. To the reaction solution was added saturated aqueous sodium hydrogen carbonate and the mixture was vigorously stirred. The organic layer was separated and concentrated under reduced pressure. The residue was purified by NH-silica gel column (Fuji Silysia Chemical Lyd., Pro. No. DM1020, eluting solvent: ethyl acetate) to give the title compound (25.7 g) as a viscous oil.

Workup

  1. stirringthe mixture was vigorously stirred
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by NH-silica gel column (Fuji Silysia Chemical Lyd
  5. washDM1020, eluting solvent

Sources & evidence

ORD record
ord-b025d315912149dbabd12f93e307ebcf
Source dataset
uspto-grants-2007_02
Patent number
US07183415B2

Reaction notes

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