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Benzoic Acid → N-(7-methoxy-1,8-naphthyridin-2-yl)benzamide

HRID 235807
Notes
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Reaction equation

HRID 235807 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][CH3:22])=[CH:16][CH:17]=2)[N:12]=1.C(#N)C>O>[CH3:22][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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 6342AcetonitrileHCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Product 1

HCID 20217526N-(7-methoxy-1,8-naphthyridin-2-yl)benzamideYield 39.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with benzoic acid (13.4 g), N,N'carbonyldiimidazole (17.8 g) and 2-amino-7-methoxy-1,8naphthyridine (12.3 g). The product produced by precipitation in water (20 g; m.p. 80° C.) is dissolved in boiling acetonitrile (200 cc). After 1 hour's cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (2×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-methoxy-1,8-naphthyridin-2-yl)benzamide (7.8 g) is produced, m.p. 134° C. EXAMPLE 10

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with acetonitrile (2×10 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-970bc17f4bbc4904b5862410cee692a7
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04642308

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes