4-Methoxybenzoic Acid → HCID 20217553, compound

HRID 235838Notes

Reaction equation

HRID 235838 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([O:23][C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:31])=[CH:18][CH:19]=2)[N:14]=1>O>[CH3:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([CH3:30])[C:24]=1[O:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 20217518HCID 20217518, compound

Product 1

HCID 20217553HCID 20217553, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (16.7 g), N,N'-carbonyldiimidazole (17.8 g) and 2-amino-7-(2,6-dimethylphenoxy)-1,8-naphthyridine (21.2 g). The reaction mixture is poured into water and extracted with methylene chloride. After concentration of the organic phases to dryness under reduced pressure (4 kPa), the solid residue (33 g) is dissolved in boiling acetone (170 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetone (10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). By recrystallisation of the solid produced (11.5 g; m.p. approximately 100° C.) in acetone (50 cc), N-[7-(2,6-dimethylphenoxy)-1,8-naphthyridin-2-yl]-4-methoxybenzamide (9.1 g) is produced, m.p. 174° C.

Workup

  1. extractionextracted with methylene chloride
  2. dissolutionAfter concentration of the organic phases to dryness under reduced pressure (4 kPa), the solid residue (33 g) is dissolved
  3. customthe crystallised solid is separated by filtration
  4. washwashed with acetone (10 cc)
  5. customdried at 40° C. under reduced pressure (0.067 kPa)
  6. customBy recrystallisation of the solid
  7. customproduced (11.5 g; m.p. approximately 100° C.) in acetone (50 cc)

Sources & evidence

ORD record
ord-433f9886ac404815a3a66ead971afbdd
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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