3-[(ethoxycarbonyl)amino]benzoic acid → HCID 13983397, compound

HRID 580479Notes

Reaction equation

HRID 580479 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O)=[O:5])[CH3:2].[NH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[N:20][C:21]([O:27][CH3:28])=[CH:22][CH:23]=2)[N:18]=1>O>[CH3:28][O:27][C:21]1[N:20]=[C:19]2[C:24]([CH:25]=[CH:26][C:17]([NH:16][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=3)=[N:18]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7176623-[(ethoxycarbonyl)amino]benzoic acidHCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Product 1

HCID 13983397HCID 13983397, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 3-ethoxycarbonylaminobenzoic acid (10 g), N,N'-carbonyldiimidazole (7.6 g) and 2-amino-7-methoxy-1,8-naphthyridine (5.95 g). The reaction mixture is then poured into water (1000 cc) and the precipitate formed is separated by filtration, washed with water (10 cc) and dried in the air. On recrystallization in ethyl acetate (100 cc) of the product thereby obtained, N-(7-methoxy-1,8-naphthyridin-2-yl)-3-ethoxycarbonylaminobenzamide (7.3 g), m.p. 120° C., is obtained.

Workup

  1. customthe precipitate formed
  2. customis separated by filtration
  3. washwashed with water (10 cc)
  4. customdried in the air
  5. customOn recrystallization in ethyl acetate (100 cc) of the product
  6. customthereby obtained

Sources & evidence

ORD record
ord-2fa9986e06394ad09bc13329c7a98702
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

Loading…