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

HRID 1487734Notes

Reaction equation

HRID 1487734 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-9016577e1d5241c4a3b45686845d9848
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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