Benzoyl chloride → HCID 13579402, compound

HRID 235806Notes

Reaction equation

HRID 235806 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([Cl:12])=[CH:7][CH:8]=2)[N:3]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[Cl:12][C:6]1[N:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([NH:1][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579402HCID 13579402, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 2-amino-7-chloro-1,8-naphthyridine (5.4 g) in pyridine (60 cc), benzoyl chloride (4.2 g) is added slowly, maintaining the temperature in the region of 30° C. After the solution has been maintained for 3 hours at a temperature in the region of 20° C., the product is precipitated in distilled water (340 cc). The solid produced after drying in the air is dissolved in boiling ethanol (88 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×5 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)benzamide (4.95 g) is thus produced, m.p. 198° C. EXAMPLE 9

Workup

  1. temperatureAfter the solution has been maintained for 3 hours at a temperature in the region of 20° C.
  2. customthe product is precipitated in distilled water (340 cc)
  3. customThe solid produced
  4. customafter drying in the air
  5. dissolutionis dissolved
  6. temperatureAfter 3 hours' cooling at 4° C.
  7. customthe crystallised solid is separated by filtration
  8. washwashed with ethanol (2×5 cc)
  9. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-6824298046394ccbaaab286c281237d1
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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