Ethyl chloroformate → HCID 69992103, compound

HRID 1797108Notes

Reaction equation

HRID 1797108 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[C:11]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][N:12]=1.[CH2:18]([O:20][C:21](Cl)=[O:22])[CH3:19]>N1C=CC=CC=1>[CH2:18]([O:20][C:21](=[O:22])[NH:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:16]=1)[CH3:19]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 9834439HCID 9834439, compound

Product 1

HCID 69992103HCID 69992103, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl-amine (0.80 g, 3.6 mmol) in pyridine (20 ml) was cooled to 0° C. and ethylchloroformate (0.47 g, 4.3 mmol) was slowly added. Stirring was continued for 72 hr. Then the solvent was evaporated and the residue was partitioned (AcOEt/H2O). The organic phase was dried (MgSO4), concentrated and chromatographed (SiO2 with CH2Cl2/CH3OH=98/2) to give the title compound (0.36 g, 36%) as a yellow oil. MS: m/e=294 (M+).

Workup

  1. customThen the solvent was evaporated
  2. customthe residue was partitioned (AcOEt/H2O)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (SiO2 with CH2Cl2/CH3OH=98/2)

Sources & evidence

ORD record
ord-9ca7250396a04a088b5ebbcac795806e
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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