4-Methoxy-2-quinolinecarboxylic acid → HCID 178492678, compound

HRID 1580062Notes

Reaction equation

HRID 1580062 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:5]([C:6](O)=[O:7])[CH:4]=1.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:5]([C:6]([NH:16][C:17]2[NH:21][N:20]=[N:19][N:18]=2)=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 5945964-Methoxy-2-quinolinecarboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178492678HCID 178492678, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxyquinaldic acid (7.25 g) was dissolved in dry dimethylformamide (20 ml). N,N'-carbonyldiimidazole (5.8 g) was added, and the solution was stirred for 6 hours at room temperature. 5-Aminotetrazole (3.69 g) was added and the mixture was stirred overnight at room temperature. The solid was filtered off, washed with methanol and dissolved in dimethylformamide (500 ml) with the minimum addition of dimethylaminoethanol to effect dissolution. Water (50 ml) was added, and the solution was adjusted to pH 2 by the addition of aqueous hydrochloric acid. The solid was filtered off to give 4-methoxy-N(1H-tetrazol-5-yl)quinaldamide, m.p. 289° (d).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe solid was filtered off
  3. washwashed with methanol
  4. dissolutiondissolved in dimethylformamide (500 ml) with the minimum addition of dimethylaminoethanol
  5. dissolutiondissolution
  6. additionWater (50 ml) was added
  7. additionthe solution was adjusted to pH 2 by the addition of aqueous hydrochloric acid
  8. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-97f9888969cb4efb829f8ea2e2ac07d4
Source dataset
uspto-grants-1976_01
Patent number
US03932416

Reaction notes

Loading…