Isatin → HCID 178488823, compound

HRID 1170879Notes

Reaction equation

HRID 1170879 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][C:23](O)=[O:24])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C([O-])(=[O:28])C.[Na+]>CC(O)=O>[OH:24][C:23]1[C:22]([C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)=[C:4]([C:2]([OH:28])=[O:3])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 517045Sodium Acetate

Product 1

HCID 178488823HCID 178488823, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of isatin (2.21 g, 15 mmol), 3,4-dimethoxyphenylacetic acid (4.91 g, 25 mmol) and sodium acetate (0.3 g) was heated at 200° C. for 3 hrs (TLC monitoring). After cooling, the mixture was added with AcOH (100 mL), and the precipitate was collected, washed with H2O, and dried to give 2-hydroxy-3-[(3,4-dimethoxy)phenyl]quinoline-4-carboxylic acid as a crude intermediate, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate was collected
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-6741d2ac78ce40ab815de3c11a5ca873
Source dataset
uspto-grants-2010_11
Patent number
US07829567B2

Reaction notes

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