Beta-Alanine → HCID 20392989, compound

HRID 1862992Notes

Reaction equation

HRID 1862992 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[NH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].C(=O)([O-])O.[Na+].Cl>COCCO>[C:6]([C:5]1[CH:14]=[CH:15][C:2]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:3]([N+:16]([O-:18])=[O:17])[CH:4]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 417434-Chloro-3-nitrobenzophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 20392989HCID 20392989, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

4-Chloro-3-nitrobenzophenone (10 g.) was added to a mixture of 3-aminopropionic acid (β-alanine) (10.1 g.) and sodium hydrogen carbonate (9.6 g.) in 2-methoxyethanol (100 ml.) which was then heated under reflux for 4 hours. The mixture was cooled, poured into ice-water (250 ml.) and brought to pH 3 by addition of concentrated hydrochloric acid. The solid obtained was filtered, washed with water and air-dried to give 3-(4-benzoyl-2-nitroanilino)propionic acid (12.1 g), m.p. 170°-5° C.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-852afe11ac9e41bba06d43f0914faf83
Source dataset
uspto-grants-1979_09
Patent number
US04167569

Reaction notes

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