Phenylacetic Acid → HCID 13787379, compound

HRID 2413926Notes

Reaction equation

HRID 2413926 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.C(#N)C>O>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 6342AcetonitrileHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787379HCID 13787379, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with phenylacetic acid (10.9 g), N,N'-carbonyldiimidazole (13 g) and 2-amino-7-chloro-1,8-naphthyridine (10.8 g). The product obtained by precipitation in water (13.5 g; m.p. 184° C.) is dissolved in boiling acetonitrile (210 cc). After cooling for 1 hour at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (10 cc) and dried at 45° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)phenylacetamide (11.3 g), m.p. 187° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with acetonitrile (10 cc)
  4. customdried at 45° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-c5cf96a8d5644ff4a3a1d5e31417d446
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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