Diethyl Ether → HCID 21584300, compound

HRID 369937Notes

Reaction equation

HRID 369937 reaction equation
[ClH:1].[OH:2][CH:3]1[CH2:9][C:8]2[CH:10]=[CH:11][C:12]([N+:14]([O-])=O)=[CH:13][C:7]=2[CH2:6][NH:5][CH2:4]1.CCOCC>C(O)C>[ClH:1].[OH:2][CH:3]1[CH2:9][C:8]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:7]=2[CH2:6][NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 21584392HCID 21584392, compound

Product 1

HCID 21584300HCID 21584300, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 4-hydroxy-8-nitro-2,3,4,5-tetrahydro-1H-2-benzazepine hydrochloride (1.80 g, 7.36 mmol) (G. L. Grunewald and V. H. Dahanukar, J. Heterocycl. Chem., 1994, 31, 1609) and 5% Pd--C (0.2 g) in ethanol (100 ml) was hydrogenated at 50 psi for 2 h. The catalyst was filtered off and the solvent was concentrated to give a solid. This solid was dissolved in hot ethanol (50 ml) and ether (200 ml) was added slowly. The solid was collected, washed with ether (100 ml) and air-dried to give the title compound as a yellow solid (1.44 g, 91%), m.p. 232.5-4° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solvent was concentrated
  3. customto give a solid
  4. customThe solid was collected
  5. washwashed with ether (100 ml)
  6. customair-dried

Sources & evidence

ORD record
ord-2c113a57b0d349a7bdbe730af0ec1dcd
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

Loading…