Ethanol → HCID 20217531, compound

HRID 235831Notes

Reaction equation

HRID 235831 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][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[F:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C:17]2[N:16]=[C:15]3[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=4)=[N:14]3)=[CH:19][CH:18]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 74784-Methoxybenzoic AcidHCID 20217533HCID 20217533, compound

Product 1

HCID 20217531HCID 20217531, compoundYield 73.3%

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 (14.3 g), N,N'-carbonyldiimidazole (15.2 g) and 2-amino-7-(4-fluorophenoxy)-1,8-naphthyridine (15.2 g). The product produced by precipitation in water (22.6 g; m.p. approximately 70° C.) is dissolved in boiling ethanol (130 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×15 cc) and dried at 25° C. under reduced pressure (0.067 kPa). N-[7-(4-fluorophenoxy)-1,8-naphthyridin-2-yl]-4-methoxybenzamide (17 g) is produced, m.p. 100° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with ethanol (2×15 cc)
  4. customdried at 25° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-04084420bae549c1b09029f9984209c0
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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