Phosgene → 5-Isocyanatoisoquinoline

HRID 887186Notes

Reaction equation

HRID 887186 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:5]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2)=[C:1]=[O:2]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 707665-Aminoisoquinoline

Product 1

HCID 115863575-Isocyanatoisoquinoline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Phosgene (20 ml, 20% in toluene from Fluka) in CH2Cl2 (300 mL) at 0° C. was treated with DMAP (10 g) in CH2Cl2 (100 mL) slowly. After complete addition, the mixture was treated with 5-aminoisoquinoline (5 g) in CH2Cl2 (100 mL) dropwise. The mixture was allowed to warm to room temperature and then stirred overnight. The solvent was removed under reduced pressure. The solid residue was extracted with diethyl ether (400 mL). The diethyl ether was filtered to provide the title compound in diethyl ether as a pale yellow solution. The diethyl ether solution was used in subsequent reactions without further purification.

Workup

  1. additionAfter complete addition
  2. customThe solvent was removed under reduced pressure
  3. extractionThe solid residue was extracted with diethyl ether (400 mL)
  4. filtrationThe diethyl ether was filtered

Sources & evidence

ORD record
ord-6a60d50e6b4243b6851fe8823c945b71
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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