2,6-Dimethylaniline → HCID 44366397, compound

HRID 729100Notes

Reaction equation

HRID 729100 reaction equation
Cl.[CH3:2][C:3]1[C:12]([CH2:13][CH2:14]Cl)=[C:11](Cl)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:17][C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:19]=1[NH2:20]>CC(O)C>[CH3:17][C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:19]=1[N:20]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([CH3:2])[C:12]=2[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 67906098HCID 67906098, compound

Product 1

HCID 44366397HCID 44366397, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-methyl-3-(2-chloroethyl)-4-chloroquinoline hydrochloride (13.8 g, 50 mmol), 2,6-dimethylaniline (12.5 ml, 100 mmol) and 2-propanol (400 ml) was heated to 140° for 5 days in a pressure vessel, then cooled and evaporated. The crude product was converted to free base and chromatographed (silica gel, methanolic ammonia in dichloromethane). Recrystallisation from aqueous methanol followed by aqueous ethanol gave 1-(2,6-dimethylphenyl)-4-methyl- 2,3-dihydropyrrolo[3,2-c]quinoline (1.52 g), m.p. 149°-152°.

Workup

  1. temperaturewas heated to 140° for 5 days in a pressure vessel
  2. temperaturecooled
  3. customevaporated
  4. customchromatographed (silica gel, methanolic ammonia in dichloromethane)
  5. customRecrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-29436ab7d0c64ec1a7f2983220eb89e9
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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