3-Methoxybenzoic Acid → N-(7-methoxy-1,8-naphthyridin-2-yl)-3-methoxybenzamide

HRID 235821Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=2)[N:14]=1>O.C(#N)C>[CH3:24][O:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 3-methoxybenzoic acid (9.1 g), N,N'-carbonyldiimidazole (9.7 g) and 2-amino-7-methoxy-1,8-naphthyridine (7 g). The product produced by precipitation in water (13 g; m.p. approximately 75° C.) is dissolved in 90 cc of boiling acetonitrile. After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (3×10 cc) and dried at 50° C. under reduced pressure (0.067 kPa). N-(7-methoxy-1,8-naphthyridin-2-yl)-3-methoxybenzamide (8.7 g) is produced, m.p. 135° C.).

Workup

customthe crystallised solid is separated by filtration
washwashed with acetonitrile (3×10 cc)
customdried at 50° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record: ord-afdf05b3660c40568dffc0b8ee8ae755
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642308

Reaction notes

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