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

HRID 1068638Notes

Reaction equation

HRID 1068638 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-64d0928846ae4eecae9fe8064280d20d
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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