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

HRID 1668996Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of N-(6-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 6-nitro-5-indanamine 2 (0.69 g, 95%) as an orange solid: 1H NMR δ 7.93 (s, 1H, H-7), 6.64 (s, 1H, H-4), 5.99 (br s, 2H, NH2), 2.79-2.88 (m, 4H, H-1, H-3), 2.02-2.10 (m, 2H, H-2); 13C NMR δ 154.3, 144.2, 134.0, 131.3, 120.8, 113.5, 33.0, 31.4, 25.7.

Workup

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

Sources & evidence

ORD record: ord-bb994a13cbbe4ef79a681b8951979556
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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