Sodium borohydride → HCID 20217551, compound

HRID 235861Notes

Reaction equation

HRID 235861 reaction equation
[CH:1]([C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH:13][C:14](=[O:23])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[N:10]2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH:13][C:14](=[O:23])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20217524HCID 20217524, compound

Product 1

HCID 20217551HCID 20217551, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-(7-formyl-1,8-naphthyridin-2-yl)-4-methoxybenzamide (6.65 g) in methanol (150 cc), sodium borohydride (0.41 g) is added during 15 minutes at 20° C., and the mixture is left stirred for 1 hour at 20° C. until the evolution of gas has ceased. The suspension produced is poured into distilled water (800 cc) which is acidified to pH 4 with acetic acid. The solid obtained by filtration and drying (6.15 g; m.p. 212° C.) is dissolved in boiling dioxane (180 cc). After the mixture has been cooled for 3 hours at a temperature in the region of 20° C., the crystallised solid is separated by filtration, washed with dioxane (2×15 cc) and dried at 50° C. under reduced pressure (0.067 kPa). N-(7-Hydroxymethyl-1,8-naphthyridin-2-yl)-4-methoxybenzamide (4.4 g) is produced, m.p. 218° C.

Workup

  1. waitthe mixture is left
  2. customThe suspension produced
  3. additionis poured
  4. distillationinto distilled water (800 cc) which
  5. customThe solid obtained by filtration
  6. customdrying (6.15 g; m.p. 212° C.)
  7. dissolutionis dissolved
  8. temperatureAfter the mixture has been cooled for 3 hours at a temperature in the region of 20° C.
  9. customthe crystallised solid is separated by filtration
  10. washwashed with dioxane (2×15 cc)
  11. customdried at 50° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-e2c05b3f60ae4f608ca84083b2516e96
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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