HCID 178524696, compound → HCID 178516363, compound

HRID 1578379Notes

Reaction equation

HRID 1578379 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O>N1C2C(=CC=CC=2)C=CC=1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178524696HCID 178524696, compound

Product 1

HCID 178516363HCID 178516363, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

A mixture of 17 g (73 mmoles) of 4-hydroxy-6,7-methylenedioxyquinoline-3-carboxylic acid, ref. 3 g, of Cu powder and 100 ml of quinoline was heated at reflux for one-half hour at an internal temperature of 235°-240°. The mixture was filtered, cooled and diluted with 250 ml of Skelly C. Filtration of the resultant precipitate yielded a light brown solid, mp 276°-279° dec. Recrystallizations from EtOH gave 9.1 g of the quinoline, mp 280°-281° C dec. ref. D. Kaminsky and R. I. Meltzer, U.S. Pat. No. 3,287,458. (Nov. 22, 1966) [Chem. abstr. 66, 65399 u (1967)].

Workup

  1. temperatureat reflux for one-half hour at an internal temperature of 235°-240°
  2. filtrationThe mixture was filtered
  3. temperaturecooled
  4. additiondiluted with 250 ml of Skelly C
  5. filtrationFiltration of the resultant precipitate
  6. customyielded a light brown solid, mp 276°-279° dec
  7. customRecrystallizations from EtOH

Sources & evidence

ORD record
ord-f241ee179cd44d60b938c0691666f403
Source dataset
uspto-grants-1976_02
Patent number
US03936461

Reaction notes

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