Ammonia → 8-methoxyquinoline-5-carboxylic Acid

HRID 2393079Notes

Reaction equation

HRID 2393079 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].O[CH2:14][CH:15]([CH2:17]O)O.N.C>S(=O)(=O)(O)O.O.II>[CH3:12][O:11][C:10]1[C:2]2[N:1]=[CH:17][CH:15]=[CH:14][C:3]=2[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 297MethaneHCID 753GlycerolHCID 178233-Amino-4-methoxybenzoic acid

Product 1

HCID 102622888-methoxyquinoline-5-carboxylic AcidYield 69.3%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A of 3-amino-4-methoxybenzoic acid (5.0 g), glycerol (4.16 g), and iodine (135 mg) in concentrated sulphuric acid (5 ml) was heated at 180° C. for 2 hours. The reaction was allowed to cool, diluted with water (170 ml), made basic to pH8/9 with 0.88 ammonia and stirred with activated charcoal (2.0 g). The mixture was filtered through Celite and the filtrate acidified to pH4/5 with acetic acid. The precipitate was obtained by filtration and dried in a dessicator to yield the desired product (4.21 g) as a tan solid.

Workup

  1. temperatureto cool
  2. filtrationThe mixture was filtered through Celite
  3. customThe precipitate was obtained by filtration
  4. customdried in a dessicator

Sources & evidence

ORD record
ord-c2d23ffb56d34a55b891331cec52ab79
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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