Methanol → HCID 13983413, compound

HRID 580494Notes

Reaction equation

HRID 580494 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[NH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[N:11][C:12]([Cl:18])=[CH:13][CH:14]=2)[N:9]=1.C(N(CC)CC)C.CO>C(Cl)Cl>[Cl:18][C:12]1[N:11]=[C:10]2[C:15]([CH:16]=[CH:17][C:8]([NH:7][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[N:9]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983413HCID 13983413, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

Methacryloyl chloride (9 g) dissolved in methylene chloride (30 cc) is added in the course of 20 minutes to a solution of 2-amino-7-chloro-1,8-naphthyridine (9 g) and triethylamine (19 g) in methylene chloride (300 cc). After 30 minutes' heating under reflux, the solution obtained is washed with 0.5 N hydrochloric acid (150 cc) and distilled water (2×150 cc) and then concentrated to dryness under reduced pressure (4 kPa). The solid obtained (13.5 g) is dissolved in boiling methanol (350 cc). After 3 hours' cooling at 4° C., the crystallized solid is separated by filtration, washed with methanol (2×30 cc) and dried in the air. The isolated product (9 g; m.p. 195° C.) is then added in the course of 5 minutes to concentrated sulphuric acid (d=1.83; 19 cc). The reaction mixture is heated for 10 minutes to 60° C., stirred for 1 hour at 25° C. and then poured into distilled water (200 cc). The precipitate formed is separated by filtration, washed with distilled water (5×20 cc) and recrystallized in acetonitrile (70 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)methacrylamide (5.4 g), m.p. 182° C., is thereby obtained.

Workup

  1. temperatureAfter 30 minutes' heating
  2. temperatureunder reflux
  3. customthe solution obtained
  4. washis washed with 0.5 N hydrochloric acid (150 cc)
  5. distillationdistilled water (2×150 cc)
  6. concentrationconcentrated to dryness under reduced pressure (4 kPa)
  7. customThe solid obtained (13.5 g)
  8. dissolutionis dissolved
  9. customthe crystallized solid is separated by filtration
  10. washwashed with methanol (2×30 cc)
  11. customdried in the air
  12. additionThe isolated product (9 g; m.p. 195° C.) is then added in the course of 5 minutes to concentrated sulphuric acid (d=1.83; 19 cc)
  13. temperatureThe reaction mixture is heated for 10 minutes to 60° C.
  14. additionpoured
  15. distillationinto distilled water (200 cc)
  16. customThe precipitate formed
  17. customis separated by filtration
  18. washwashed with distilled water (5×20 cc)
  19. customrecrystallized in acetonitrile (70 cc)

Sources & evidence

ORD record
ord-73012a488ec04984a5828d440c9de435
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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