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

HRID 1600756Notes

Reaction equation

HRID 1600756 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-da3e71205fa24b05917833f0a28d879b
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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