Benzaldehyde → Benzyl-(4-chloro-2-methylquinolin-6-yl)amine

HRID 408652Notes

Reaction equation

HRID 408652 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:12].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH2:13]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:21])[CH:6]=[C:5]2[Cl:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 687284244-Chloroquinolin-6-amine

Product 1

HCID 68729251Benzyl-(4-chloro-2-methylquinolin-6-yl)amine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

6-Amino-4-chloroquinoline (0.1 g; see step (ii) above), benzaldehyde (0.055 g) and sodium tnacetoxyborohydride (0.22 g) in 1,2-dichloroethane was stirred overnight. The mixture was diluted with dichloromethane and washed with water then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane. The desired fractions were concentrated and the sample evaporated to dryness to give the title compound as an oil.

Workup

  1. washwashed with water
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane
  6. concentrationThe desired fractions were concentrated
  7. customthe sample evaporated to dryness

Sources & evidence

ORD record
ord-d4edff718eee47328fd49349f899fec7
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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