4-Chlorobutyryl chloride → HCID 66620109, compound

HRID 415518Notes

Reaction equation

HRID 415518 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[NH2:12].[Cl:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>ClCCCl>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]([NH:12][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=2)=[O:18]

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chlorideHCID 666199614-Chloro-1,5-naphthyridin-3-amine

Product 1

HCID 66620109HCID 66620109, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-chloro[1,5]naphthyridin-3-amine (2.0 g, 11 mmol) and 4-chlorobutyryl chloride (4.7 g, 33 mmol) in 1,2-dichloroethane (75 mL) was heated at reflux for 20 hours. The reaction mixture was then concentrated under reduced pressure and the residue washed with two 25 mL portions of hexane. The solid was then taken up in methanol (35 mL), 1.0 mL of 10% solution of sodium hydroxide in water was added, and the solution was stirred at room temperature for 4 hours. The reaction mixture was then concentrated under reduced pressure to provide 4-chloro-N-(4-chloro[1,5]naphthyridin-3-yl)butanamide which was used directly in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. washthe residue washed with two 25 mL portions of hexane
  5. addition1.0 mL of 10% solution of sodium hydroxide in water was added
  6. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f1d9f5421b444c0a23c14a28b7ac1db
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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