Ethanol → HCID 13787391, compound

HRID 2413935Notes

Reaction equation

HRID 2413935 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]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[NH: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)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 74784-Methoxybenzoic AcidHCID 13787376HCID 13787376, compound

Product 1

HCID 13787391HCID 13787391, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 4-methoxybenzoic acid (6.1 g), N,N'-carbonyldiimidazole (6.5 g) and 2-amino-7-anilino-1,8-naphthyridine (7 g). The product obtained by precipitation in water (12 g) is dissolved in boiling ethanol (140 cc). After cooling for 1 hour at 4° C., the crystallized solid is separated by filtration, washed with ethanol (10 cc), and dried at 45° C. under reduced pressure (0.07 kPa). N-(7-Anilino-1,8-naphthyridin-2-yl)-4-methoxybenzamide (4.5 g), m.p. 245° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with ethanol (10 cc)
  4. customdried at 45° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-5a797eaf26f74792a71249d689b533c1
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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