Glycerol → 8-Bromo-5,6,7-trimethylquinoline

HRID 235590Notes

Reaction equation

HRID 235590 reaction equation
[Br:1][C:2]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([CH3:11])=[CH:5][C:3]=1[NH2:4].O[CH2:13][CH:14]([CH2:16]O)O.O=[As](O[As](=O)=O)=O.S(=O)(=O)(O)O>O.N>[Br:1][C:2]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([CH3:11])=[C:5]2[C:3]=1[N:4]=[CH:16][CH:14]=[CH:13]2

Participants

7

Reactant 4

HCID 753Glycerol2×HCID 1118Sulfuric AcidHCID 14771Arsenic pentoxideHCID 139354182-Bromo-3,4,5-trimethylaniline

Product 1

HCID 139354168-Bromo-5,6,7-trimethylquinoline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-3,4,5-trimethylaniline (10.4 g), glycerol (4 equiv) and arsenic oxide (0.75 equiv) were stirred and heated to 100° C. Concentrated sulfuric acid (60% w/w of the glycerol) was added to the mixture dropwise. After heating at 130° C. for 4 hr, the cooled mixture was diluted with water and neutralised with aqueous ammonia. The solid was filtered off, washed with water and dried in air. Purification by column chromatography over alumina with dichloromethane elution gave 8-bromo-5,6,7-trimethylquinoline as a white solid, mp 180° C. Pmr spectrum (CDCl3 ; δ in ppm): 2.50 (3H,s); 2.61 (3H,s); 2.74 (3H,s); 7.37-8.98 (3H,m).

Workup

  1. temperatureAfter heating at 130° C. for 4 hr
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customdried in air
  5. customPurification by column chromatography over alumina
  6. washwith dichloromethane elution

Sources & evidence

ORD record
ord-831306daf7884cffbfdae75e7d3620a3
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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