N-methyl-2-pyrrolidone → 2-Hydroxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthalene

HRID 1069813Notes

Reaction equation

HRID 1069813 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([O:19][CH3:20])=[CH:6][C:4]=1[NH2:5].[CH3:21][N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27].[OH:28][C:29]1[C:38]([C:39](Cl)=[O:40])=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:42](Cl)=[O:43])[CH:35]=2)[CH:30]=1>C1(C)C=CC=CC=1>[OH:28][C:29]1[C:38]([C:39]([NH:5][C:4]2[CH:6]=[C:7]([O:19][CH3:20])[C:8]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:3]=2[O:2][CH3:1])=[O:40])=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:42]([NH:5][C:4]3[CH:6]=[C:7]([O:19][CH3:20])[C:21]([NH:22][C:23](=[O:27])[C:24]4[CH:13]=[CH:12][CH:11]=[CH:26][CH:25]=4)=[CH:9][C:3]=3[O:2][CH3:1])=[O:43])[CH:35]=2)[CH:30]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 804424-Benzoylamino-2,5-dimethoxyanilineHCID 18551881HCID 18551881, compound

Product 1

HCID 211919812-Hydroxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthaleneYield 81.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

2,5-Dimethoxy-4-benzoylaminoaniline (16.6 g), N-methyl-2-pyrrolidone (111.2 g) and toluene (30.1 g) were dissolved at room temperature and the acid chloride (5.5 g) obtained in Example 6 was gradually added, and then the mixture was amidated according to Example 8. After the reaction solution was cooled to 25° C. and filtered, toluene was distilled off under reduced pressure. Then, the solution was crystallized by using methanol (377.2 g). The resultant product was subjected to reflux washing using methanol (250.0 g) for 1 hour, filtered and then dried to obtain 12.4 g of 2-hydroxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenyl-aminocarbonyl)naphthalene as a dull yellow powdered crystal (DSC analysis value: 327.4° C.).

Workup

  1. filtrationfiltered
  2. distillationtoluene was distilled off under reduced pressure
  3. customThen, the solution was crystallized
  4. temperatureto reflux
  5. washwashing
  6. customfor 1 hour
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-7c2cec3f21134bee9757be832d870f87
Source dataset
uspto-grants-2001_06
Patent number
US06252104B1

Reaction notes

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