Diisopropyl Ether → HCID 13983412, compound

HRID 580493Notes

Reaction equation

HRID 580493 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[NH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[N:10][C:11]([Cl:17])=[CH:12][CH:13]=2)[N:8]=1.C(N(CC)CC)C.C(OC(C)C)(C)C>C(Cl)Cl>[Cl:17][C:11]1[N:10]=[C:9]2[C:14]([CH:15]=[CH:16][C:7]([NH:6][C:1](=[O:4])[CH:2]=[CH2:3])=[N:8]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983412HCID 13983412, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (42 g) is added with stirring in the course of 30 minutes to a solution of 2-amino-7-chloro-1,8-naphthyridine (54 g) and triethylamine (115 g) in methylene chloride (1875 cc). The solution obtained is heated for 1 hour under reflux and then poured into isopropyl ether (5000 cc). The precipitate obtained is filtered off, washed with isopropyl ether (3×200 cc) and then water (3×200 cc) at 40° C. and dried in the air. The crude product obtained is purified by flash chromatography (under 50 kPa) on a column 60 mm in diameter containing silica (500 g; 0.04-0.06 mm), eluting with a mixture (99:1 by volume) of methylene chloride and methanol and collecting 100-cc fractions. After concentration of fractions 5 to 10 to dryness at 40° C. under reduced pressure (4 kPa), N-(7-chloro-1,8-naphthyridin-2-yl)acrylamide (5.85 g), m.p. 200° C., is obtained.

Workup

  1. customThe solution obtained
  2. temperatureis heated for 1 hour
  3. temperatureunder reflux
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with isopropyl ether (3×200 cc)
  7. dry with materialwater (3×200 cc) at 40° C. and dried in the air
  8. customThe crude product obtained
  9. customis purified by flash chromatography (under 50 kPa) on a column 60 mm in diameter
  10. additioncontaining silica (500 g; 0.04-0.06 mm)
  11. washeluting with a mixture (99:1 by volume) of methylene chloride and methanol
  12. customcollecting 100-cc fractions

Sources & evidence

ORD record
ord-9a8a5cfed5bd4312b5f165c20af66d5d
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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