Acetic Acid → HCID 178438397, compound

HRID 1638972Notes

Reaction equation

HRID 1638972 reaction equation
[Cl-].[NH4+].C(O)(=O)C.[CH3:7][CH:8]([C:10]1[CH:17]=[C:16]2[N:12]([NH:13][C:14]([CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)=[N:15]2)[N:11]=1)[CH3:9].[OH-].[Na+]>O.CC(O)C>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][CH2:18][C:14]2[NH:13][N:12]3[N:11]=[C:10]([CH:8]([CH3:9])[CH3:7])[CH:17]=[C:16]3[N:15]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 178438398HCID 178438398, compound

Product 1

HCID 178438397HCID 178438397, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

Reduced iron (6.7 g), ammonium chloride (0.53 g) and acetic acid (0.57 ml) were added to a mixed solvent of 2-propanol (40 ml) and water (8 ml), and the resulting mixture was heated over a steam bath and refluxed. To the mixture was further added the Nitro Compound (C) obtained in the step (3) above (6.27 g) and the reflux was further continued for 30 minutes. Sodium hydroxide (3.0 g) was dissolved in water (30 ml) and this solution was added to the above mixture. The resulting mixture was stirred and then filtered to remove insolubles. To the filtrate was added water (100 ml) and acetic acid (5 ml) and the resultant mixture was stirred. The resulting precipitated crystals were filtered and washed with water and dried to obtain 5.37 g (95%) of Amino Compound (D) as pale orange crystals (m.p.: 143.5°-144.5° C.).

Workup

  1. temperaturethe resulting mixture was heated over a steam bath
  2. temperaturerefluxed
  3. customobtained in the step (3) above (6.27 g)
  4. additionthis solution was added to the above mixture
  5. filtrationfiltered
  6. customto remove insolubles
  7. additionTo the filtrate was added water (100 ml) and acetic acid (5 ml)
  8. stirringthe resultant mixture was stirred
  9. customThe resulting precipitated crystals
  10. filtrationwere filtered
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-1ceddad740bd41bfa69fa54487b24be4
Source dataset
uspto-grants-1989_11
Patent number
US04882266

Reaction notes

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