Methanol → HCID 20154401, compound

HRID 2413942Notes

Reaction equation

HRID 2413942 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[C:21](C2C=CC=CC=2OC)=[CH:20][C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[CH3:30][OH:31]>O>[CH3:30][O:31][C:2]1[CH:3]=[CH:4][CH:8]=[CH:9][C:10]=1[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

Participants

5

Reactant 3

HCID 887MethanolHCID 114563-Bromobenzoic acidHCID 20154393HCID 20154393, compound

Product 1

HCID 20154401HCID 20154401, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 11, but starting with 3-bromobenzoic acid (1.6 g), N,N'-carbonyldiimidazole (1.3 g) and 2-amino(2-methoxyphenyl)-1,8-naphthyridine (1.3 g). The product obtained by precipitation in water (1.5 g) is dissolved in boiling methanol (75 cc). After cooling for 2 hours at 4° C., the crystallized solid is separated by filtration, washed with methanol (3×3 cc) and dried at 35° C. under reduced pressure (0.07 kPa). N-[7-(2-Methoxyphenyl)-1,8-naphthyridin-2-yl]-3-bromobenzamide (0.6 g), m.p. 110° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with methanol (3×3 cc)
  4. customdried at 35° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-124ff50a546148e894a1b855bcd4ed79
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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