Acetonitrile → HCID 13579418, compound

HRID 235820Notes

Reaction equation

HRID 235820 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]([CH3:23])=[CH:18][CH:19]=2)[N:14]=1.C(#N)C>O>[CH3:23][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

5

Reactant 3

HCID 6342AcetonitrileHCID 74784-Methoxybenzoic AcidHCID 5944207-methyl-1,8-naphthyridin-2-amine

Product 1

HCID 13579418HCID 13579418, compoundYield 72.6%

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 (12.2 g), N,N'-carbonyldiimidazole (10.3 g) and 2-amino-7-methyl-1,8-naphthyridine (9.5 g). The product produced by precipitation in water (14.4 g; m.p. 110° C.) is dissolved in boiling acetonitrile (150 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (2×10 cc) and dried at 45° C. under reduced pressure (0.067 kPa). N-(7-methyl-1,8-naphthyridin-2-yl)-4-methoxybenzamide (12.7 g) is produced, m.p. 119° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with acetonitrile (2×10 cc)
  4. customdried at 45° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-b5f3edb173cb4e62a85524d54e1a16a5
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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