4-Nitrophenyl chloroformate → 4-nitrophenyl 2,3-dihydro-1H-inden-5-ylcarbamate

HRID 70158

Reaction equation

HRID 70158 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:13]>C(Cl)Cl>[CH2:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:12](=[O:13])[O:14][C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 90496Indan-5-amine

Product 1

HCID 152372784-nitrophenyl 2,3-dihydro-1H-inden-5-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Aminoindan (212 mg, 1.59 mmol) was dissolved in CH2Cl2 (10 mL), p-nitrophenyl chloroformate (417 mg, 2.07 mmol) was added, and the reaction mixture was stirred at rt overnight. The solid was removed by filtration (discarded), and the filtrate was concentrated under reduced pressure. This gave the title compound as a grey solid which was about 50% pure and was used without further purification. LC-MS: RT=9.98 min, [M+H]+=299.1.

Workup

  1. customThe solid was removed by filtration (discarded)
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9676e16e40bc47fe918cc08e4df9cd8f
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Linked notes

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