1-Chloroethyl chloroformate → 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride

HRID 1713122Notes

Reaction equation

HRID 1713122 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([Cl:18])[CH:12]=[CH:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>C(Cl)CCl>[ClH:18].[Cl:18][C:13]1[CH:12]=[CH:11][C:10]2[CH2:9][NH:8][CH2:17][CH2:16][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 162287476-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 184491652-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine (98 mg, 0.38 mmol) and 1-chloroethyl chloroformate (0.05 mL, 0.46 mmol) in ClCH2CH2Cl (10 mL) is refluxed for 3 hr. The solvent is removed and the residue is dissolved in MeOH (10 mL) and the mixture is reflux for 30 min. Solvent is removed in vacuo and the residue is stirred with ether (10 mL) for 30 min at rt and filtered. The resulting light brown solid is used in the next step without further purification. MS (M+1): 169.1.

Workup

  1. temperatureis refluxed for 3 hr
  2. customThe solvent is removed
  3. dissolutionthe residue is dissolved in MeOH (10 mL)
  4. temperaturethe mixture is reflux for 30 min
  5. customSolvent is removed in vacuo
  6. filtrationfiltered
  7. customThe resulting light brown solid is used in the next step without further purification

Sources & evidence

ORD record
ord-61d04bec5bf443a5be92d9634b722e5b
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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