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

HRID 1781049Notes

Reaction equation

HRID 1781049 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 2N 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-c56d610317f54b7aa67c4261f2a9a716
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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