Benzoic Acid → HCID 13983466, compound

HRID 580458Notes

Reaction equation

HRID 580458 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:16][CH:17]=2)[N:12]=1.O>C(OCC)(=O)C>[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][O:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:1](=[O:9])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:12]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 962WaterHCID 13983446HCID 13983446, compound

Product 1

HCID 13983466HCID 13983466, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with benzoic acid (5.5 g), N,N'-carbonyldiimidazole (8.1 g) and 2-amino-7-(2-dimethylaminoethoxy)-1,8-naphthyridine (11.6 g), heating for 5 hours under reflux. The reaction mixture is poured into water (1500 cc) and extracted with ethyl acetate (2×1000 cc). After concentration of the organic phases to dryness under reduced pressure (4 kPa), the oily residue obtained (9.2 g) is dissolved in boiling ethyl acetate (25 cc). Then, after 2 hours' cooling at 4° C., the crystallized solid is separated by filtration, washed with ethyl acetate (3 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(2-Dimethylaminoethoxy)-1,8-naphthyridin-2-yl]benzamide (4.5 g), m.p. 109° C., is obtained.

Workup

  1. temperatureheating for 5 hours
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate (2×1000 cc)
  4. customAfter concentration of the organic phases to dryness under reduced pressure (4 kPa), the oily residue obtained (9.2 g)
  5. dissolutionis dissolved
  6. customthe crystallized solid is separated by filtration
  7. washwashed with ethyl acetate (3 cc)
  8. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-148b42066bcd44daa05db04e06397dd3
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

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