Ethanol → HCID 20217534, compound

HRID 235833Notes

Reaction equation

HRID 235833 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]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[O: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 702EthanolHCID 74784-Methoxybenzoic AcidHCID 20217510HCID 20217510, compound

Product 1

HCID 20217534HCID 20217534, compoundYield 64.4%

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 (16.4 g), N,N'-carbonyldiimidazole (17.5 g) and 2-amino-7-(2-chlorophenoxy)-1,8-naphthyridine (18.5 g). The product produced by precipitation in water (28 g; m.p. approximately 80° C.) is dissolved in boiling ethanol (800 cc). After 15 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×20 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-[7-(2-chlorophenoxy)-1.8-naphthyridin-2-yl]-4-methoxybenzamide (17.8 g) is produced, m.p 190° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with ethanol (2×20 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-4e30f4cfce2f46d2a095c94fdd586c56
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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