Formic Acid → HCID 23453298, compound

HRID 1277722Notes

Reaction equation

HRID 1277722 reaction equation
[NH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:8]=1)[NH2:2].[CH:16]([O-])=[O:17].[Na+].C(O)=O>C(O)C>[CH:16]([NH:2][NH:1][C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:8]=1)=[O:17]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 2723810Sodium FormateHCID 234533055-Hydrazinyl-2-methoxybenzenepropanoic acid

Product 1

HCID 23453298HCID 23453298, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(5-Amino-2-methoxyphenyl)propionic acid (4 g, 0.02 mole), concentrated hydrochloric acid (30 ml) and water (45 ml) were stirred together at 0°. The mixture was treated with sodium nitrite (1.38 g, 0.02 mole) in water (10 ml) at 0°. The solution was then stirred for a further one-half hour. The excess of nitrous acid was destroyed with urea. The above reaction mixture was added to a solution of stannous chloride (7.6 g) in concentrated hydrochloric acid (10 ml). The precipitate (5 g) was collected by filtration. Free hydrazine was obtained from a concentrated aqueous solution of the crude hydrochloride by addition of saturated aqueous solution of sodium acetate. A mixture of 3-(5-hydrazino-2-methoxyphenyl)propionic acid (8.8 g, 0.025 mole), sodium formate (2.8 g, 0.04 mole), formic acid (18 ml) and ethanol (60 ml) was heated under reflux for one hour. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate (1 liter). The organic layer was then washed with water and dilute aqueous hydrochloric acid (1 percent). The organic layer was dried with sodium sulphate, the solvent was removed under reduced pressure and the residue crystallized from water (5 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. customThe solvents were removed under vacuum
  4. dissolutionthe residue was dissolved in ethyl acetate (1 liter)
  5. washThe organic layer was then washed with water and dilute aqueous hydrochloric acid (1 percent)
  6. dry with materialThe organic layer was dried with sodium sulphate
  7. customthe solvent was removed under reduced pressure
  8. customthe residue crystallized from water (5 g)

Sources & evidence

ORD record
ord-4746caa36223432dbc4bbd9dc131e59a
Source dataset
uspto-grants-1981_07
Patent number
US04278748

Reaction notes

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