1-Propanol → HCID 54021780, compound

HRID 2413927Notes

Reaction equation

HRID 2413927 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([Cl:23])=[CH:18][CH:19]=2)[N:14]=1.C(O)CC>N1C=CC=CC=1>[Cl:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:1](=[O:10])[CH:2]=[CH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 660233-Phenylprop-2-enoyl chlorideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 54021780HCID 54021780, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

Cinnamoyl chloride (7.3 g) is added to a suspension of 2-amino-7-chloro-1,8-naphthyridine (7.2 g) in pyridine (80 cc). After stirred for 2 hours at 20° C., the suspension obtained is poured into distilled water (500 cc). The suspension is filtered, washed with water (3×50 cc) and dried at 50° C. under reduced pressure (0.07 kPa). The solid obtained (10.6 g; m.p. 263° C.) is dissolved in boiling 1-propanol (1200 cc). After cooling for 4 hours at 4° C., the crystallized solid is separated by filtration, washed with 1-propanol (3×50 cc), diethyl ether (2×50 cc) and dried at 50° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-3-phenylpropenamide (11.4 g), m.p. 263° C., is obtained.

Workup

  1. customthe suspension obtained
  2. additionis poured
  3. distillationinto distilled water (500 cc)
  4. filtrationThe suspension is filtered
  5. washwashed with water (3×50 cc)
  6. customdried at 50° C. under reduced pressure (0.07 kPa)
  7. customThe solid obtained (10.6 g; m.p. 263° C.)
  8. dissolutionis dissolved
  9. temperatureAfter cooling for 4 hours at 4° C.
  10. customthe crystallized solid is separated by filtration
  11. washwashed with 1-propanol (3×50 cc), diethyl ether (2×50 cc)
  12. customdried at 50° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-66745bf915864f4ab2275a0416c939b0
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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