Quinaldic Acid → HCID 13787378, compound

HRID 2413916Notes

Reaction equation

HRID 2413916 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19]([Cl:25])=[CH:20][CH:21]=2)[N:16]=1>CN(C)C=O.CO>[Cl:25][C:19]1[N:18]=[C:17]2[C:22]([CH:23]=[CH:24][C:15]([NH:14][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[O:13])=[N:16]2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7124Quinaldic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787378HCID 13787378, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 2-quinolinecarboxylic acid (10.4 g), N,N'-carbonyldiimidazole (13 g) and 2-amino-7-chloro-1,8-naphthyridine (7.2 g). After cooling at 4° C., the crystallized solid is separated by filtration, washed with distilled water (5×50 cc) and air-dried. The product obtained (7.4 g; m.p. 260° C.) is dissolved in a mixture of dimethylformamide (200 cc) and methanol (200 cc). After cooling for 3 hours at 4° C., the crystallized solid is separated by filtration, washed with methanol (3×15 cc) and dried at 35° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)quinoline-2-carboxamide (3.6 g), m.p. 275° C., is obtained.

Workup

  1. customthe crystallized solid is separated by filtration
  2. washwashed with distilled water (5×50 cc)
  3. customair-dried
  4. customThe product obtained (7.4 g; m.p. 260° C.)
  5. temperatureAfter cooling for 3 hours at 4° C.
  6. customthe crystallized solid is separated by filtration
  7. washwashed with methanol (3×15 cc)
  8. customdried at 35° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-e16d13c8706642ad9852f41065107695
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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