Anthranilic Acid → HCID 67132180, compound

HRID 1663077Notes

Reaction equation

HRID 1663077 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]=O)=[CH:13][CH:12]=1>CO>[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]=[N:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 780724-Quinolinecarboxaldehyde

Product 1

HCID 67132180HCID 67132180, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of anthranilic acid (5.46 g) in methanol was added to a melt of quinoline-4-carbaldehyde (6.26 g) and the mixture was heated on a water bath for 6 hours. The mixture was cooled to room temperature and the solid material was isolated by filtration and washed with methanol, affording 2-[(quinolin-4-ylmethylene)-amino]-benzoic acid (10.33 g). This intermediate (10.3 g) was dissolved in THF and ethanol, and sodium borohydride (1.41 g) was added portion-wise. The reaction mixture was stirred at room temperature for 3 hours. More sodium borohydride (1.41 g) and a small amount of methanol were added and stirring continued at room temperature for 4 hours. The mixture was evaporated under reduced pressure and transferred to a separatory funnel with EtOAc and water. Layers were separated and the aqueous layer was neutralised by addition of 4M hydrochloric acid. The resulting precipitated material was isolated by filtration, washed with water and dried in vacuo, affording the title compound (7.1 g). 13C-NMR (DMSO-d6) δ 170.4, 150.3, 150.3, 147.6, 144.8, 133.4, 131.7, 129.6, 129.2, 126.5, 126.1, 123.5, 118.5, 114.6, 112.9, 111.2, 42.7.

Workup

  1. temperaturethe mixture was heated on a water bath for 6 hours
  2. customthe solid material was isolated by filtration
  3. washwashed with methanol

Sources & evidence

ORD record
ord-a93304be12bd4b53833ed2341a8da468
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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