Water → HCID 23372626, compound

HRID 1898878Notes

Reaction equation

HRID 1898878 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)=[O:4].Cl[C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].O>C(OCCO)CCC>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]2[NH:11][C:14]3[N:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16](=[O:17])[NH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 762582-Chloronicotinic acidHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 23372626HCID 23372626, compound

Reagents, catalysts & solvents 1

HCID 81332-ButoxyethanolSolvent

Conditions

Temperature
140 °C

Procedure

A stirred mixture of 1.66 g (0.010 mol) of 4-methoxycarbonyl-o-phenylene-diamine and 1.58 g (0.010 mol) of 2-chloronicotinic acid in 5 ml of 2-butoxyethanol was heated to 140° C. for 2 h, during which time a dark solution, followed by formation of a green solid, was observed. The reaction mixture was poured into 50 ml of water and the solid collected and stirred in 10% sodium carbonate solution for 1 h. The resulting solid was collected, washed thoroughly with water, dried and crystallized from DMF to yield 1.1 g (40% of theory) of a beige crystalline product, m.p. 344°-349° C.

Workup

  1. customthe solid collected
  2. customThe resulting solid was collected
  3. washwashed thoroughly with water
  4. customdried
  5. customcrystallized from DMF
  6. customto yield 1.1 g (40% of theory) of a beige crystalline product, m.p. 344°-349° C.

Sources & evidence

ORD record
ord-42804322c1d749fab9dd22582eb32721
Source dataset
uspto-grants-1996_11
Patent number
US05571809

Reaction notes

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