Acetic Acid → HCID 19864295, compound

HRID 1199917Notes

Reaction equation

HRID 1199917 reaction equation
Cl.[CH3:2][N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([N+:13]([O-])=O)[S:12][C:6]=2[CH:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:4]1.[C:22](O)(=[O:24])[CH3:23]>[Pd].C(OC(=O)C)(=O)C>[C:22]([NH:13][C:11]1[S:12][C:6]2[CH:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:4][N:3]([CH3:2])[CH2:9][CH2:8][C:7]=2[CH:10]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19864290HCID 19864290, compound

Product 1

HCID 19864295HCID 19864295, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 6-methyl-2-nitro-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine hydrochloride (0.20 g) and 10% palladium on carbon (20 mg) in acetic acid (18 ml), acetic anhydride (2 ml) was hydrogenated on a Parr apparatus for 24 hours at 70 psi. The mixture was filtered and the filtrate evaporated. The residue was dissolved in water (30 ml), basified to pH~11 with ammonia solution and extracted with dichloromethane (2×50 ml). The extracts were dried filtered and evaporated to a yellow viscous oil. Crystallisation from toluene gave the title product (m.p. 180°).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in water (30 ml)
  4. extractionextracted with dichloromethane (2×50 ml)
  5. customThe extracts were dried
  6. filtrationfiltered
  7. customevaporated to a yellow viscous oil
  8. customCrystallisation from toluene

Sources & evidence

ORD record
ord-04ae26713f964af3a658a4e843df0333
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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