Nitrobenzene → HCID 20028938, compound

HRID 2118615Notes

Reaction equation

HRID 2118615 reaction equation
N[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].[N+](C1C=CC=CC=1)([O-])=[O:18]>>[CH2:13]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2](=[O:18])[CH:3]=[C:4]1[CH3:12])[CH:14]=[CH2:15]

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 7841Allyl bromideHCID 811164-Amino-2-methylquinoline

Product 1

HCID 20028938HCID 20028938, compound

Procedure

The starting material was prepared as follows. A solution of 4-amino-2-methylquinoline (5.0 g.) and allyl bromide (3.32 ml.) in nitrobenzene (13.7 ml.) was stirred at 100° for 1 hour. The reaction mixture was cooled to below 5° and the resulting precipitate filtered off, washed with ether and dried. A suspension of this material in N aqueous NaOH (75 ml.) was stirred at 100° for 3.5 hours. The cooled mixture was extracted with EtOAc (2×75 ml.) and the combined extracts washed, dried and evaporated to give 1-allyl-2-methyl-4-quinolone. Reaction of this compound with toluene-p-sulphonyl chloride gave 1-allyl-4-chloro-2-methylquinolinium toluene-p-sulphonate.

Workup

  1. customThe starting material was prepared
  2. temperatureThe reaction mixture was cooled to below 5°
  3. filtrationthe resulting precipitate filtered off
  4. washwashed with ether
  5. customdried
  6. additionA suspension of this material in N aqueous NaOH (75 ml.)
  7. extractionThe cooled mixture was extracted with EtOAc (2×75 ml.)
  8. washthe combined extracts washed
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-89b9c9aeffe34e5288d7a02ee0799948
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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