3-Bromobenzoic acid → HCID 13787382, compound

HRID 2413917Notes

Reaction equation

HRID 2413917 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:18]=2)[N:13]=1>O.C(#N)C>[O:22]([C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)=[N:13]2)=[CH:18][CH:17]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 114563-Bromobenzoic acidHCID 137873732-Amino-7-phenoxy-1,8-naphthyridine

Product 1

HCID 13787382HCID 13787382, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 3-bromobenzoic acid (6 g), N,N'-carbonyldiimidazole (4.9 g) and 2-amino-7-phenoxy-1,8-naphthyridine (5.9 g). The product obtained by precipitation in water (9.8 g; m.p. 188°-192° C.) is dissolved in acetonitrile (300 cc). After cooling for 1 hour at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (3×10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-(7-Phenoxy-1,8-naphthyridin-2-yl)-3-bromobenzamide (5.4 g), m.p. 194° C., is obtained.

Workup

  1. customthe crystallized solid is separated by filtration
  2. washwashed with acetonitrile (3×10 cc)
  3. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-7d9a0d1a8cf44d19ac664b4eda712b5c
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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