4-Nitrobenzaldehyde → HCID 18359235, compound

HRID 428700Notes

Reaction equation

HRID 428700 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:13])[C:11]#[CH:12])=[CH:6][CH:5]=1)([O-])=O.C([Mg]Cl)#C.[N+](C1C=CC(C=O)=CC=1)([O-])=O.[Cl-].[NH4+]>CO.[Zn].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:13])[C:11]#[CH:12])=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 25517Ammonium ChlorideHCID 1329051-(4-Nitrophenyl)prop-2-yn-1-olHCID 178462451HCID 178462451, compound

Product 1

HCID 18359235HCID 18359235, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(4-Nitro-phenyl)-2-propyn-1-ol (4.89 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 4-nitrobenzaldehyde (Aldrich) according to method A above) was added to 10% H2O in methanol (150 mL) and to this mixture was added zinc dust (44.01 mmol) and ammonium chloride (10.67 mmol). The reaction was heated at reflux for 3 h, at which time the reaction was cooled and the solid was filtered off. The solids were washed extensively with ethyl acetate, and the ethyl acetate and methanol were evaporated in vacuo. The resulting precipitate was filtered off, dried and recrystallized from ethyl acetate/hexane to yield 1-(4-amino-phenyl)-2-propyn-1-ol.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h, at which time the reaction
  3. temperaturewas cooled
  4. filtrationthe solid was filtered off
  5. washThe solids were washed extensively with ethyl acetate
  6. customthe ethyl acetate and methanol were evaporated in vacuo
  7. filtrationThe resulting precipitate was filtered off
  8. customdried
  9. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5326109ac8f6446baaadd46dba193eda
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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