N-(4-nitro-2,3-dihydro-1H-inden-5-yl)acetamide → 4-Nitro-5-indanamine

HRID 1668997Notes

Reaction equation

HRID 1668997 reaction equation
[N+:1]([C:4]1[C:12]([NH:13]C(=O)C)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH2:8]2)([O-:3])=[O:2]>Cl.O>[N+:1]([C:4]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH2:8]2)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 12887049N-(4-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 128870504-Nitro-5-indanamineYield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of N-(4-nitro-2,3-dihydro-1H-inden-5-yl)acetamide (0.90 g, 4.09 mmol) in 5 M HCl was heated at 100° C. for 16 h. The suspension was cooled to 20° C., diluted with water (100 mL), filtered, washed with water (3×15 mL) and dried to give 4-nitro-5-indanamine 3 (Schroeder, E, et al., European J. Med. Chem. 1982, 17, 35) (0.69 g, 95%) as an orange solid: mp (H2O) 105-107° C.; 1H NMR δ 7.17 (d, J=8.2 Hz, 1H, H-7), 6.62 (d, J=8.2 Hz, 1H, H-6), 5.73 (br s, 2H, NH2), 3.32 (br t, J=7.5 Hz, 2H, H-3), 2.80-2.85 (m, 2H, H-1), 2.02-2.11 (m, 2H, H-2). Anal. calcd for C9H10N2O2: C, 60.7; H, 5.7; N, 15.7. Found: C, 60.5; H, 5.5; N, 15.8%.

Workup

  1. temperatureThe suspension was cooled to 20° C.
  2. filtrationfiltered
  3. washwashed with water (3×15 mL)
  4. customdried

Sources & evidence

ORD record
ord-e3ec16979ebb4c17921d533f95e3a85d
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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