4-Nitrobenzoic Acid → HCID 178526538, compound

HRID 2218419Notes

Reaction equation

HRID 2218419 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[CH:4][N:3]=1.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=O)=[CH:16][CH:15]=1)([O-:13])=[O:12]>O=P(Cl)(Cl)Cl>[Cl:10][C:5]1[C:6]([Cl:9])=[C:7]2[N:8]=[C:18]([C:17]3[CH:21]=[CH:22][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 454802354,5-Dichloropyridine-2,3-diamine

Product 1

HCID 178526538HCID 178526538, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
105 °C

Procedure

2,3-Diamino-4,5-dichloropyridine (Example 206a) (2.5 g, 14 mmol) and 4-nitrobenzoic acid (2.3 g, 14 mmol) were dissolved in POCl3 (40 ml) and heated to 105° C. for 5 h. The excess of POCl3 was evaporated off and the residue was dissolved in EtOAc and aqueous K2CO3. The aqueous phase was basified with 10M KOH and extracted three times with EtOAc. The combined organic phase was washed with brine, dried (Na2SO4) and evaporated in vacuo to afford the title compound (2.5 g, 58%).

Workup

  1. customThe excess of POCl3 was evaporated off
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionextracted three times with EtOAc
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d5739230cc7e407e8100b55e8596a384
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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