Methyl Chloride → HCID 2912688, compound

HRID 2049556Notes

Reaction equation

HRID 2049556 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[NH:3]1.[C:15](Cl)(=[O:19])[C:16](Cl)=[O:17].CCl>C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4]3=[C:5]([C:15](=[O:19])[C:16](=[O:17])[N:3]13)[CH:6]=[C:7]([CH3:13])[CH:8]=2

Participants

5

Reactant 3

HCID 6327Methyl ChlorideHCID 65578Oxalyl chlorideHCID 2940622,2,4,6-tetramethyl-1,2-dihydroquinoline

Product 1

HCID 2912688HCID 2912688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2-Dihydro-2,2,4,6-tetramethylquinoline (16.7 g., 0.09 mole) in 50 ml. dry methylene chloride was added slowly dropwise with stirring to oxalyl chloride (12.6 g., 0.1 mole) in 150 ml. dry methyl chloride under nitrogen at 30° C. Addition required 20 min., and when complete the very dark solution was stirred 15 min. at ambient temperature and one hour at a gentle reflux. The solvent was removed at reduced pressure and the dark red residue crystallized from methanol to yield a solid melting at 157°-161° C. Two additional recrystallizations from 25% chloroform in ligroine (60°-110° C.) gave a deep red crystalline solid melting at 163.5°-165.5° C. The yield was 44%.

Workup

  1. customat 30° C
  2. additionAddition required 20 min., and when complete the very dark solution
  3. customThe solvent was removed at reduced pressure
  4. customthe dark red residue crystallized from methanol

Sources & evidence

ORD record
ord-7f39d7b05ac34462b8dbbd61f7242e4f
Source dataset
uspto-grants-1980_04
Patent number
US04198414

Reaction notes

Loading…