4-Methoxybenzoic Acid → HCID 13983416, compound

HRID 580497Notes

Reaction equation

HRID 580497 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([C:23]#[N:24])=[CH:18][CH:19]=2)[N:14]=1>>[C:23]([C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[N:14]2)=[CH:19][CH:18]=1)#[N:24]

Participants

3

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 20134006HCID 20134006, compound

Product 1

HCID 13983416HCID 13983416, compoundYield 11.3%

Procedure

The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (8.2 g), N,N'-carbonyldiimidazole (8.7 g) and 2-amino-7-cyano-1,8-naphthyridine (6.9 g), and heating for 4 hours under reflux. The insoluble product is separated by filtration and the filtrate is poured into water (1000 cc). The resulting precipitate is filtered off, washed with water (3×75 cc) and dried in the air. The solid obtained is purified by flash chromatography (under 30 kPa) on a column 40 mm in diameter containing silica (170 g; 0.04-0.06 mm), eluting with pure methylene chloride and collecting 50-cc fractions. After concentration of fractions 5 to 27 to dryness at 40° C. under reduced pressure (4 kPa), the product obtained is purified by recrystallization in dioxane (160 cc). N-(7-Cyano-1,8-naphthyridin-2-yl)-4-methoxybenzamide (1.4 g), m.p. 283° C., is thereby obtained.

Workup

  1. temperatureheating for 4 hours
  2. temperatureunder reflux
  3. customThe insoluble product is separated by filtration
  4. additionthe filtrate is poured into water (1000 cc)
  5. filtrationThe resulting precipitate is filtered off
  6. washwashed with water (3×75 cc)
  7. customdried in the air
  8. customThe solid obtained
  9. customis purified by flash chromatography (under 30 kPa) on a column 40 mm in diameter
  10. additioncontaining silica (170 g; 0.04-0.06 mm)
  11. washeluting with pure methylene chloride
  12. customcollecting 50-cc fractions
  13. customAfter concentration of fractions 5 to 27 to dryness at 40° C. under reduced pressure (4 kPa), the product obtained
  14. customis purified by recrystallization in dioxane (160 cc)

Sources & evidence

ORD record
ord-7c05057446cc4d3caad0ead9b0d1ae16
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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