Acetonitrile → HCID 13579417, compound

HRID 235819Notes

Reaction equation

HRID 235819 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]([Br:23])=[CH:18][CH:19]=2)[N:14]=1.C(#N)C>O>[Br: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 6342AcetonitrileHCID 74784-Methoxybenzoic AcidHCID 20217560HCID 20217560, compound

Product 1

HCID 13579417HCID 13579417, compoundYield 46.4%

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 (10.2 g), N,N'-carbonyldiimidazole (10.8 g) and 2-amino-7-bromo-1,8-naphthyridine (11.2 g). The product produced by precipitation in water (9.8 g; m.p. 220° C.) is dissolved in boiling acetonitrile (1000 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (2×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-bromo-1,8-naphthyridin-2-yl)-4-methoxybenzamide (8.3 g) is produced, m.p. 221° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with acetonitrile (2×10 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-a28f5eb1856142948a38f4b29f0a8820
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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