Acetic Acid → HCID 21543500, compound

HRID 1606504Notes

Reaction equation

HRID 1606504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[C:12]([N+]([O-])=O)[CH3:13].C(O)(=[O:19])C.S(=O)(O)[O-].[Na+]>CC(C)=O.O.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12](=[O:19])[CH3:13]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 23665763Sodium BisulfiteHCID 53815307HCID 53815307, compound

Product 1

HCID 21543500HCID 21543500, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 104g of 5-chloro-3-(2-nitropropen-1-yl)indole, 115g of powdered iron and 6g of ferric chloride dissolved in 1250 ml of acetone is brought to reflux. Heating ceases as soon as reflux commences and a solution of 265 ml of acetic acid in 800 ml of water is added over 30 minutes. The reaction mixture is again brought to reflux and maintained thereat for 4 hours; 25.6g of sodium bisulphite are then added, the mixture cooled to 20°C and filtered. The residue is washed with acetone. The combined filtrate and washings are concentrated after filtering and redissolved in 105 ml of hydrochloric acid and 520 ml of water, extracted with ethyl acetate, washed and dried.

Workup

  1. temperatureto reflux
  2. temperatureHeating ceases as soon as reflux commences
  3. temperatureto reflux
  4. temperaturemaintained
  5. filtrationfiltered
  6. washThe residue is washed with acetone
  7. concentrationThe combined filtrate and washings are concentrated
  8. filtrationafter filtering
  9. dissolutionredissolved in 105 ml of hydrochloric acid
  10. extraction520 ml of water, extracted with ethyl acetate
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-6901a14d5e2840658e0a62571182b73f
Source dataset
uspto-grants-1976_04
Patent number
US03953442

Reaction notes

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