Beta-Alanine → HCID 131712089, compound

HRID 1414047Notes

Reaction equation

HRID 1414047 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=1[NH2:7].[NH2:13][CH2:14][CH2:15][C:16](O)=O.[ClH:19]>O>[OH2:1].[ClH:12].[ClH:19].[OH:1][CH2:2][CH2:3][N:4]1[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=2[N:7]=[C:16]1[CH2:15][CH2:14][NH2:13].[OH:1][CH2:2][CH2:3][N:4]1[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=2[N:7]=[C:16]1[CH2:15][CH2:14][NH2:13].[ClH:12].[ClH:12]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 10702726HCID 10702726, compound

Product 1

HCID 131712089HCID 131712089, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.7 g. (52 mmole) 2-(2-hydroxyethylamino)-4-chloroaniline, 6.9 g. (78 mmole) β-alanine, 46 ml. concentrated hydrochloric acid and 54 ml. of water is heated at reflux with stirring for 24 hrs. After cooling, the solution is concentrated, and made basic with 10% aqueous sodium hydroxide. Continuous liquid-liquid extraction of the aqueous solution with ethyl acetate affords 9.9 g. of the product, which is converted to it hydrochloride salt. The product has a m.p. of 196°-200° C. after recrystallization from methanol/ethyl acetate.

Workup

  1. additionA mixture of 9.7 g
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. concentrationthe solution is concentrated
  5. extractionContinuous liquid-liquid extraction of the aqueous solution with ethyl acetate
  6. customaffords 9.9 g
  7. customafter recrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-ce287dd9e96447b59bbacfc21df204dd
Source dataset
uspto-grants-1981_02
Patent number
US04252816

Reaction notes

Loading…