HCID 15087420, compound → HCID 178468488, compound

HRID 345389Notes

Reaction equation

HRID 345389 reaction equation
[C:1]([NH:8][C:9]1[CH:22]=[CH:21][C:12]2[S:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:11]=2[C:10]=1[N+:23]([O-])=O)([C:3](OCC)=[O:4])=[O:2]>C(O)C.[Pd]>[CH2:19]([O:18][C:16]([C:14]1[S:13][C:12]2[CH:21]=[CH:22][C:9]3[N:8]=[C:1]([OH:2])[C:3]([OH:4])=[N:23][C:10]=3[C:11]=2[CH:15]=1)=[O:17])[CH3:20]

Participants

4

Reactant 1

HCID 15087420HCID 15087420, compound

Product 1

HCID 178468488HCID 178468488, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-ethoxalylamino-2-ethoxycarbonyl-4-nitrobenzo[b]thiophene (0.84 g, 2.3 mmol) in ethanol was hydrogenated at atmospheric pressure and room temperature in the presence of 0.55 g of 5% palladium-on-charcoal. The catalyst was removed by filtration and washed with ethanol. The filtrate was heated to reflux for 11/2 h, and cooled. The resulting precipitate was collected by filtration and washed with ethanol to give 0.42 g (63%) of the title compound, m.p. 357°-36l° C.; IR (KBr): 1680 cm-1 ; 1H-NMR (DMSO-d6) 1.36 (t, J=7 Hz, 3H, CH3), 4.37 (q, J=7 Hz, 2H, CH2), 7.33 (d, J=g Hz, 1H, ArH), 7.73 (d, J=g Hz, 1H, ArH), 8.83 (s, 1H, H-9), 12.06 and 12.30 (2 broad s, 2H, 2 OH).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol
  3. temperatureThe filtrate was heated
  4. temperatureto reflux for 11/2 h
  5. temperaturecooled
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-885090f85158445ea7177776a9c8e069
Source dataset
uspto-grants-1991_10
Patent number
US05057516

Reaction notes

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