Isonicotinic Acid → HCID 22058004, compound

HRID 1828714Notes

Reaction equation

HRID 1828714 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](C(Cl)=O)=[CH:3][CH:2]=1.N1C=CC([C:16](O)=[O:17])=CC=1.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:43])[C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[CH:29]=[CH:30][C:31]=1[Cl:32]>O.N1C=CC=CC=1>[Cl:32][C:31]1[CH:30]=[CH:29][C:28]([NH:33][C:34](=[O:43])[C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)=[CH:27][C:26]=1[NH:25][C:16]([C:5]1[CH:6]=[N:1][CH:2]=[CH:3][CH:4]=1)=[O:17]

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 65578Oxalyl chlorideHCID 417436Pyridine-4-carbonyl chlorideHCID 16793499HCID 16793499, compound

Product 1

HCID 22058004HCID 22058004, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of pyrid-4-ylcarbonyl chloride (prepared by the reaction of pyridine-4-carboxylic acid and oxalyl chloride; 0.213 g), N-(3-amino-4-chlorophenyl)-4-cyanobenzamide (0.27 g) and pyridine (4 ml) was stirred and heated to 110° C. for 16 hours. After cooling, the mixture was poured into water (25 ml). The resultant precipitate was collected, washed with water and dried to give the title compound as a solid (0.32 g); NMR Spectrum: (DMSOd6) 7.58 (d, 1H), 7.75 (m, 1H), 7.85 (d, 2H), 8.01 (d, 2H), 8.10 (m, 3H), 8.80(d, 2H); Mass Spectrum: M+H+ 377.

Workup

  1. temperatureAfter cooling
  2. customThe resultant precipitate was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b5b008267099449f8f07bed173460859
Source dataset
uspto-grants-2006_06
Patent number
US07060700B2

Reaction notes

Loading…