O-Toluidine → HCID 44366324, compound

HRID 729082Notes

Reaction equation

HRID 729082 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH3:17].[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21]>C(O)C>[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[N:21]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([O:16][CH3:17])[C:8]=3[N:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 54522485HCID 54522485, compound

Product 1

HCID 44366324HCID 44366324, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(3-chloropropyl)-4-chloro-8-methoxyquinoline (6.4 g, 23.6 mmol) and 2-methylaniline (5.0 ml, 47.2 mmol) in ethanol (250 ml) was heated at reflux for 4 days, then cooled and evaporated. Dichloromethane and aqueous sodium bicarbonate solution were added, and the organic layer washed with water, dried and evaporated. Chromatography (silica gel, 1% methanolic ammonia in dichloromethane) followed by crystallisation from ethyl acetate gave 1-(2-methylphenyl)-7-methoxy-1,2,3,4-tetrahydropyridino-[3,2-c]quinoline (1.92 g, 27%), m.p. 160°-161°.

Workup

  1. temperatureat reflux for 4 days
  2. temperaturecooled
  3. customevaporated
  4. additionDichloromethane and aqueous sodium bicarbonate solution were added
  5. washthe organic layer washed with water
  6. customdried
  7. customevaporated
  8. customChromatography (silica gel, 1% methanolic ammonia in dichloromethane) followed by crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-1c73592508554908b974616ac6a4b4fa
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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