Hydrochloric Acid → 1-(2-Chlorophenyl)-2-nitroethanamine hydrochloride

HRID 709134Notes

Reaction equation

HRID 709134 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH:14]C(=O)OC(C)(C)C)[CH2:10][N+:11]([O-:13])=[O:12]>O1CCOCC1.ClCCl>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH2:14])[CH2:10][N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59536890tert-Butyl [1-(2-chlorophenyl)-2-nitroethyl]carbamate

Product 1

HCID 866947771-(2-Chlorophenyl)-2-nitroethanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

10 ml of a 4 N solution of hydrogen chloride in dioxane were added to a solution of 1.037 g (3.45 mmol) of tert-butyl [1-(2-chlorophenyl)-2-nitroethyl]carbamate [see, for example, Tetrahedron Lett. 2009, 50 (9), 1016] in 10 ml of dichloromethane, and the mixture was stirred at RT for 2 h. The volatile components were then removed on a rotary evaporator. 5 ml of dichloromethane were added to the residue, and the mixture was once more freed from the solvent on a rotary evaporator and then dried under high vacuum. This gave 898 mg of the title compound (quant., still contains about 8% dioxane according to 1H NMR).

Workup

  1. customThe volatile components were then removed on a rotary evaporator
  2. addition5 ml of dichloromethane were added to the residue
  3. customthe mixture was once more freed from the solvent on a rotary evaporator
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-e0511c3a006f4034b348e7f01e5c7141
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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