O-Toluidine → HCID 11726157, compound

HRID 1534363Notes

Reaction equation

HRID 1534363 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[C:17]([O:19][CH3:20])=[O:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:24][C:23]1[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=1[CH3:21])=[CH:13][CH:12]=[CH:11][C:10]=2[C:17]([O:19][CH3:20])=[O:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 10356962HCID 10356962, compound

Product 1

HCID 11726157HCID 11726157, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 3-butyryl-4-chloroquinoline-8-carboxylate (3.8 g) and 2-methylaniline (1.6 ml, 15 mmol) in 1,4-dioxan (20 ml) was heated at reflux for 30 minutes, then left to stand overnight. The solid was filtered off and washed with ethyl acetate, then converted to free base and recrystallised from methanol to obtain methyl 3-butyryl-4-(2-methylphenylamino)quinoline-8- carboxylate (2.86 g, 56%), m.p. 113-115°.

Workup

  1. temperatureat reflux for 30 minutes
  2. waitleft
  3. filtrationThe solid was filtered off
  4. washwashed with ethyl acetate
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-7d09ffab903a49ffb6690a889438d669
Source dataset
uspto-grants-1992_02
Patent number
US05089498

Reaction notes

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