Phosgene → 3-Chloro-5-isocyanatoisoquinoline

HRID 887265Notes

Reaction equation

HRID 887265 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([Cl:12])[N:6]=[CH:7]2.[C:13](Cl)(Cl)=[O:14]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[Cl:12][C:5]1[N:6]=[CH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([N:1]=[C:13]=[O:14])[CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 167490403-Chloroisoquinolin-5-amine

Product 1

HCID 223376853-Chloro-5-isocyanatoisoquinoline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

5-Amino-3-chloroisoquinoline (740 mg, 4.15 mmol) was suspended in toluene (20 mL) and treated with 20% w/v phosgene solution in toluene (9 mL) and triethylamine (5 mL). The mixture was refluxed overnight and was then concentrated in vacuo and used in the next step without further purification.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationwas then concentrated in vacuo
  3. customused in the next step without further purification

Sources & evidence

ORD record
ord-6c33b8c267a94638be4665ad47409470
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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