Hydrazine hydrate (1:1) → 6,7,8,9-Tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamine

HRID 1687242Notes

Reaction equation

HRID 1687242 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][CH2:12][CH2:11][NH:10][CH2:9][C:8]=2[CH:14]=1)([O-])=O.O.NN>C(O)C.[Pd]>[CH:14]1[C:8]2[CH2:9][NH:10][CH2:11][CH2:12][S:13][C:7]=2[CH:6]=[CH:5][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 578538112-Nitro 6,7,8,9-tetrahydro-5-thia-8-aza-benzocycloheptene

Product 1

HCID 578538726,7,8,9-Tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-nitro 6,7,8,9-tetrahydro-5-thia-8-aza-benzocycloheptene (1.0 g, 0.0047 mol), hydrazine hydrate (10 mL) in ethanol (40 mL) was added 10% palladium on carbon (0.2 g) and refluxed 3 days, filtered and concentrated to give 6,7,8,9-tetrahydro-5-thia-8-aza-benzocyclohepten-2-ylamine (0.76 g, 90%) as a yellow solid. MP: 110-111° C.; 1H-NMR (DMSO-d6) δ 7.08-15 (d, 1H), 6.45 (s, 1H), 6.25-33 (d, 1H), 5.15 (s, 2H), 3.78 (s, 2H), 3.10-20 (m, 2H), 2.50-60 (m, 2H), 2.00-22 (br, 1H); LC/MS (ESI+): 181 (M+H).

Workup

  1. temperaturerefluxed 3 days
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ee467e52bbe84d858c4f01c496fc051c
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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