4-Methoxybenzoic Acid → N-(1,8-naphthyridin-2-yl)-4-methoxybenzamide

HRID 235816Notes

Reaction equation

HRID 235816 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][CH:17]=[CH:18][CH:19]=2)[N:14]=1>O>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:21]=[CH:22][C:13]=1[NH:12][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 41730482-Amino-1,8-naphthyridine

Product 1

HCID 13579420N-(1,8-naphthyridin-2-yl)-4-methoxybenzamideYield 82.6%

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 (4.55 g), N,N'-carbonyldiimidazole (6.55 g) and 2-amino-1,8-naphthyridine (5.2 g). The product produced by precipitation in water (8.35 g; m.p. 85° C., viscous) is filtered and then dissolved in boiling 1-propanol (50 cc). After 1 hour's cooling at 4° C., the crystallised solid is separated by filtration, washed with 1-propanol (2×5 cc) and dried at 35° C. under reduced pressure (0.067 kPa). N-(1,8-naphthyridin-2-yl)-4-methoxybenzamide (6.9 g) is produced, m.p. 150° C.

Workup

  1. filtrationis filtered
  2. dissolutiondissolved
  3. customthe crystallised solid is separated by filtration
  4. washwashed with 1-propanol (2×5 cc)
  5. customdried at 35° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-3e4fb58d82824e4a934aeb3b6794f0ff
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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