Formic Acid → 3-Amino-3-(2-nitrophenyl)propionic acid

HRID 589361Notes

Reaction equation

HRID 589361 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].C(O)=O.[C:15]([OH:21])(=[O:20])[CH2:16]C(O)=O.C([O-])=O.[NH4+:25].Cl>O>[NH2:25][CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:16][C:15]([OH:21])=[O:20]

Participants

7

Reactant 5

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 111012-NitrobenzaldehydeHCID 2723923Ammonium formate

Product 1

HCID 27792173-Amino-3-(2-nitrophenyl)propionic acidYield 64.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

o-Nitrobenzaldehyde (20.4 g, 0.135 mol), formic acid (20.3 mL, 0.539 mol) and malonic acid (18.3 g, 0.176 mol) were stirred at 45° C. for half an hour. Then ammonium formate (21.3 g, 0.338 mol) was added thereto, the reaction temperature was raised to 70° C. and stirred for 1 hour, and then stirred at 95° C. for another 4 hours. Then concentrated hydrochloric acid (50 mL) was added and further stirred maintaining this temperature for another 1 hour. It was cooled. 25 mL water was added, and washed twice with ethyl acetate (2×25 mL). The aqueous phase was adjusted to pH 4.2 with 50% potassium hydroxide solution. A solid precipitated. It was pumping filtered, and dried in vacuum to obtain a yellow solid 18.33 g, at a yield of 64.6%.

Workup

  1. stirringstirred at 95° C. for another 4 hours
  2. stirringfurther stirred
  3. temperaturemaintaining this temperature for another 1 hour
  4. temperatureIt was cooled
  5. washwashed twice with ethyl acetate (2×25 mL)
  6. customA solid precipitated
  7. filtrationIt was pumping filtered
  8. customdried in vacuum

Sources & evidence

ORD record
ord-5b46d4276641465886391518d43599b7
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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