Dichloromethane → 2-(4-Chloro-[1,8]naphthyridin-2-yl)-benzonitrile

HRID 1914935Notes

Reaction equation

HRID 1914935 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH2:16])=O)[CH:3]=1.ClCCl.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>>[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]#[N:16])[CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 673629212-(4-Chloro-[1,8]naphthyridin-2-yl)-benzamide

Product 1

HCID 673645562-(4-Chloro-[1,8]naphthyridin-2-yl)-benzonitrile

Procedure

To a slurry of 970 mg (3.42 mmol) 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzamide in 10 ml dichloromethane 2.85 g (12.0 mmol) 1.26 g (5.27 mmol) methoxycarbonylsulfamoyl-triethylammonium hydroxide, inner salt, (Burgess reagent) was added. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The residue was crystallized from isopropanol yielding 2-(4-chloro-[1,8]naphthyridin-2-yl)-benzonitrile as colourless crystals; HPLC-MS: 1.94 min, [M+H] 266.

Workup

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-66d02cab24974736bdd03333f00131f8
Source dataset
uspto-grants-2013_12
Patent number
US08614226B2

Reaction notes

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