Hydrochloric Acid → HCID 54288187, compound

HRID 580462Notes

Reaction equation

HRID 580462 reaction equation
C(O[CH:6](N(C)C)[N:7]([CH3:9])[CH3:8])(C)(C)C.[CH3:13][C:14]1[N:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([NH:24][C:25](=[O:34])[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[N:21]2)=[CH:16][CH:15]=1.CN(C)C=O.Cl>C(O)C.C(OCC)C.C(Cl)(Cl)(Cl)Cl.O>[CH3:6][N:7]([CH3:9])[CH:8]=[CH:13][C:14]1[N:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([NH:24][C:25](=[O:34])[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[N:21]2)=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 13579418HCID 13579418, compound

Product 1

HCID 54288187HCID 54288187, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
130 °C

Procedure

Tert-butoxybis(dimethylamino)methane (28 g) is added to a suspension composed of N-(7-methyl-1,8-naphthyridin-2-yl)-4-methoxybenzamide (12 g) and anhydrous dimethylformamide (12 cc). The mixture is stirred for 3 hours at 130° C. The solution obtained is poured into water (100 cc) and the mixture extracted with methylene chloride (200 cc). The organic extracts are washed with water (2×100 cc), dried over magnesium sulphate and concentrated to dryness at 50° C. under reduced pressure (0.5 kPa). The amorphous residue obtained is dissolved in boiling carbon tetrachloride (100 cc). A solid is precipitated by slowly adding isopropyl ether (150 cc). The crystallized solid obtained is separated by filtration, washed with isopropyl ether (30 cc) and dried in the air. The base obtained (9.2 g; m.p. approximately 110° C.) is dissolved in ethanol (150 cc) and a 4.7N solution (20 cc) of hydrochloric acid in ethyl ether is added. The precipitate obtained is separated by filtration, washed with ethyl ether (3×30 cc) and dried at 25° C. under reduced pressure (4 kPa). The crude hydrochloride obtained is purified by recrystallization in ethanol (160 cc). N-[7-(2-Dimethylaminovinyl)-1,8-naphthyridin-2-yl]-4-methoxybenzamide in the hydrochloride state (6 g), m.p. 240° C., is thereby obtained.

Workup

  1. customThe solution obtained
  2. extractionthe mixture extracted with methylene chloride (200 cc)
  3. washThe organic extracts are washed with water (2×100 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness at 50° C. under reduced pressure (0.5 kPa)
  6. customThe amorphous residue obtained
  7. dissolutionis dissolved
  8. customA solid is precipitated by slowly adding isopropyl ether (150 cc)
  9. customThe crystallized solid obtained
  10. customis separated by filtration
  11. washwashed with isopropyl ether (30 cc)
  12. customdried in the air
  13. customThe base obtained (9.2 g; m.p. approximately 110° C.)
  14. customThe precipitate obtained
  15. customis separated by filtration
  16. washwashed with ethyl ether (3×30 cc)
  17. customdried at 25° C. under reduced pressure (4 kPa)
  18. customThe crude hydrochloride obtained
  19. customis purified by recrystallization in ethanol (160 cc)

Sources & evidence

ORD record
ord-4b5b8f12540840ad8cad2ec56a5f3203
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

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