O-Toluidine → HCID 10357805, compound

HRID 1647489Notes

Reaction equation

HRID 1647489 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][C:9]=2[OH:16])(=[O:4])[CH2:2][CH3:3].[CH3:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>O1CCOCC1>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[CH3:17])=[CH:12][CH:11]=[CH:10][C:9]=2[OH:16])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 10263493HCID 10263493, compound

Product 1

HCID 10357805HCID 10357805, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Impure 3-propanoyl-4-chloro-8-hydroxyquinoline (86 g) and 2-methylaniline (10.7 ml) in dioxan (200 ml) were warmed over a steam bath for 30 minutes, then left to stand overnight. After evaporation of the dioxan, dichloromethane and aqueous sodium bicarbonate were added, the organic layer washed with water and brine, dried and evaporated to a yellow solid. Recrystallisation from methanol gave 3-propanoyl-4-(2-methylphenylamino)-8-hydroxyquinoline (11.6 g), m.p. 125°-128°.

Workup

  1. waitleft
  2. customAfter evaporation of the dioxan, dichloromethane and aqueous sodium bicarbonate
  3. additionwere added
  4. washthe organic layer washed with water and brine
  5. customdried
  6. customevaporated to a yellow solid
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-8b14e82cbb594fed869b9a9a4b0137c4
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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