2-Methylquinoline → Quinoline, 4-nitro-

HRID 1037473Notes

Reaction equation

HRID 1037473 reaction equation
C[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:12](C1C=C(C(O)=O)C(=CC=1)C(O)=O)([O-:14])=[O:13]>[Cl-].[Zn+2].[Cl-]>[N+:12]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2][CH:11]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 70602-MethylquinolineHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

Product 1

HCID 77341Quinoline, 4-nitro-

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Using a similar reactor as in Synthesis Example 1, chinaldine (14.3 parts), 4-nitrophthalic acid (21.1 parts), zinc chloride (13.6 parts) and ODB (100 parts) were charged, followed by refluxing for 2 hours under stirring. The reaction mixture was filtered, and the filter cake was thoroughly washed with water and then dried to obtain 4-nitroquinoline. In a similar manner as in Synthesis Example 1, the 4-nitroquinoline was reduced for amination, followed by amidation with 2-bromoisobutyric acid bromide to obtain a 2-bromoisobutyric acid substitute. This will be called “Quinoline-1”. In a similar manner as in Synthesis Example 3, the structure of Quinoline-1 was confirmed by NMR and IR. By HPLC, its purity was determined to be 91.0%. By an elemental analysis, the bromine content was found to be 16.5%. A maximum absorption wavelength was measured by the spectrophotometer, and as a result, λmax=445 nm. The structural formula is shown below.

Workup

  1. additionwere charged
  2. temperatureby refluxing for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was thoroughly washed with water
  5. customdried

Sources & evidence

ORD record
ord-b5c53dd57f1544979af82ff10ef62417
Source dataset
uspto-grants-2013_10
Patent number
US08546502B2

Reaction notes

Loading…