Hydrochloric Acid → HCID 21105720, compound

HRID 131602Notes

Reaction equation

HRID 131602 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C.[Fe]>[CH2:1]([NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21105721HCID 21105721, compound

Product 1

HCID 21105720HCID 21105720, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

N1-benzyl-4-methoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (125 mg, 0.33 mmol) (from step 1) and iron powder (56 mg, 1.0 mmol) was suspended in 50% aqueous ethanol (10 ml) and reflux for 10 min. To this was added a solution of concentrated HCl (7 ul in 5 ml 50% aqueous ethanol) and refluxed for 4 h. The reaction mixture was filtered hot through celite and the filterate was basified with 15% ethanolic KOH, filtered and the filterate was concentrated in vaccuo. The residue was triturated with water, to obtain a solid which was filtered dried to give the product as white solid (90 mg) mp: 228° C.

Workup

  1. temperaturereflux for 10 min
  2. temperaturerefluxed for 4 h
  3. filtrationThe reaction mixture was filtered hot through celite
  4. filtrationfiltered
  5. concentrationthe filterate was concentrated in vaccuo
  6. customThe residue was triturated with water
  7. customto obtain a solid which
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-afb86fb42e6e4235b42eed277ff18908
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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