Hydrochloric Acid → HCID 17976006, compound

HRID 2264517Notes

Reaction equation

HRID 2264517 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:18]=[CH:17][C:13]3[O:14][CH2:15][O:16][C:12]=3[CH:11]=2)[C:5]([C:19]#[N:20])=[C:4]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1.N(OCCC(C)C)=O.[ClH:37]>C(#N)C.[Cu]Cl>[Cl:37][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:18]=[CH:17][C:13]3[O:14][CH2:15][O:16][C:12]=3[CH:11]=2)[C:5]([C:19]#[N:20])=[C:4]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 9799503HCID 9799503, compound

Product 1

HCID 17976006HCID 17976006, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

400 mg (1.08 mmol) of 2-amino-4-(1,3-benzodioxol-5-yl)-6-benzyloxy-3,5-pyridinedicarbonitrile (example 1) are dissolved in 10 ml of acetonitrile. 759 mg (0.87 ml, 6.48 mmol) of isoamyl nitrite and 871 mg (6.48 mmol) of copper(I) chloride are then added, and the mixture is stirred at 40° C. for about 16 h. The reaction solution is then diluted with 1N hydrochloric acid and extracted three times with in each case 50 ml of dichloromethane. The combined organic phases are dried with sodium sulfate and concentrated under reduced pressure. The concentration residue is crystallized from dichloromethane/methanol.

Workup

  1. extractionextracted three times with in each case 50 ml of dichloromethane
  2. dry with materialThe combined organic phases are dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe concentration residue is crystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-6adaf7ac4ba840e48a1c445a12840026
Source dataset
uspto-grants-2010_12
Patent number
US07855219B2

Reaction notes

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