Ethanol → HCID 13787386, compound

HRID 2413925Notes

Reaction equation

HRID 2413925 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[NH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[N:20][C:21]([Cl:27])=[CH:22][CH:23]=2)[N:18]=1.C(O)C>O>[Cl:27][C:21]1[N:20]=[C:19]2[C:24]([CH:25]=[CH:26][C:17]([NH:16][C:6](=[O:8])[C:5]3[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:18]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 83573,4,5-Trimethoxybenzoic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787386HCID 13787386, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 3,4,5-trimethoxybenzoic acid (17 g), N,N'-carbonyldiimidazole (13 g) and 2-amino-7-chloro-1,8-naphthyridine (8.9 g). The product obtained by precipitation in water (10.3 g; m.p. 90° C.) is dissolved in boiling ethanol (500 cc). After cooling for 4 hours at 4° C., the crystallized solid is separated by filtration, washed with ethanol (20 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-3,4,5-trimethoxybenzamide (8.2 g), m.p. 210° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with ethanol (20 cc)
  4. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-c5bf1f08ca14441f8cfd0df529683667
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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