Water → HCID 29067182, compound

HRID 1394172Notes

Reaction equation

HRID 1394172 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH:5]=[CH:6][CH:7]=1.O>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH2:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 69159049HCID 69159049, compound

Product 1

HCID 29067182HCID 29067182, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The product of Step 1 (325 mg, 1.302 mmol), was dissolved in ethanol (20 ml), and treated with iron powder (727 mg, 13.017 mmol), 20 drops of 37%. hydrochloric add and water (2 ml), and refluxed for 1 hour. The reaction was then filtered hot, and the filtrate evaporated in vacuo. The residue was dissolved in ethyl acetate then washed with saturated sodium bicarbonate solution, water, and brine, separated, dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title compound (253 mg, 88%). MS (ES+), m/e 220/222 [M+H]+.

Workup

  1. additionhydrochloric add
  2. filtrationThe reaction was then filtered hot
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthen washed with saturated sodium bicarbonate solution, water, and brine
  6. customseparated
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-f96408b03ba9447b86ee046bc394a1d2
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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