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

HRID 549695Notes

Reaction equation

HRID 549695 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-6a2c04209dec406eb5d3c941aab1dfe7
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Reaction notes

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