N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide → 6-nitro-2,3-dihydro-1H-inden-5-amine

HRID 1857429Notes

Reaction equation

HRID 1857429 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH2:10][CH2:9][CH2:8]2)(=O)C>Cl>[NH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH2:10][CH2:9][CH2:8]2

Participants

3

Reactant 1

HCID 10751392N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 27636046-nitro-2,3-dihydro-1H-inden-5-amineYield 97.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 259 mg (1.16 mmol) of 5-acetamido-6-nitroindan in 4 mL of 2 N HCl was heated at 85° C. for 9 h and cooled to room temperature. The solid precipitate was filtered, washed with water, and dried to leave 201 mg (97%) of a crystalline yellow solid. 1H NMR (CDCl3), 2.068 (m, 2), 2.843 (m, 4), 6.00 (sb, 2), 6.650 (s, 1), 7.942 (s, 1).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe solid precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bbec83df225743df92eb5bef01e308e0
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

Loading…