4-(4-Nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine → 4-(4-Aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

HRID 1939181Notes

Reaction equation

HRID 1939181 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3[S:17][CH:18]=[CH:19][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3[S:17][CH:18]=[CH:19][C:11]2=3)=[O:9])=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 153693984-(4-Nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

Product 1

HCID 214671424-(4-Aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepineYield 44.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 9.97 g of 4-(4-nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine in 110 ml of glacial acetic acid and 0.997 g of 10% palladium-on-carbon is hydrogenated in a Parr hydrogenator under 30-50 lb. of pressure for 4.5 hours. The mixture is filtered through a pad of diatomaceous earth and the filtrate concentrated to dryness under vacuum. The gummy residue (8.1 g) is purified by HPLC on a Waters-Prep-500 instrument with silica gel and ethyl acetate-hexane (1:1) as solvent. Fractions containing product are combined and the solvent removed. The residue is crystallized to give 4.0 g of crystals, m.p. 168°-172° C.

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate concentrated to dryness under vacuum
  3. customThe gummy residue (8.1 g) is purified by HPLC on a Waters-Prep-500 instrument with silica gel and ethyl acetate-hexane (1:1) as solvent
  4. additionFractions containing product
  5. customthe solvent removed
  6. customThe residue is crystallized

Sources & evidence

ORD record
ord-f525d2f73d2344c496b119fffaf7bdf5
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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