O-Toluidine → HCID 10357805, compound

HRID 1534503Notes

Reaction equation

HRID 1534503 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. Recrystallization 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. customRecrystallization from methanol

Sources & evidence

ORD record
ord-5d38bf87e70141a0a67c1e4338632fdd
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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