CID 6432229 → 6-nitro-2,3-dihydro-1H-inden-5-amine

HRID 1669007Notes

Reaction equation

HRID 1669007 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].[CH]Cl>CCO.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

5

Reactant 2

HCID 6432229CID 6432229HCID 10751392N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 27636046-nitro-2,3-dihydro-1H-inden-5-amineYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of the mixture of acetamides 17 and 18 in EtOH (400 mL) and cHCl (180 mL) was stirred at 80° C. for 6 h. The resulting solution was cooled and diluted with water (400 mL) and allowed to stand for 16 h. The precipitate was filtered, washed with water, and air-dried to give amine 2 (27.52 g, 73%, from 16) as an orange powder: mp 129-131° C. [lit. (Schroeder, E.; et al., European J. Med. Chem. 1982, 17, 35) mp (EtOH) 128.5-129.5° C.]; 1H NMR δ 7.93 (s, 1H, H-7), 6.55 (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

  1. temperatureThe resulting solution was cooled
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-e5975088710b46369fdfde6023e0503e
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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