Hydrochloric Acid → (2,4-Dimethoxy-benzylamino)-acetic acid
Reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[CH:10]=O.[OH-].[Na+].Cl>CO.[Pd]>[CH3:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[CH2:10][NH:1][CH2:2][C:3]([OH:5])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
N-(2,4-Dimethoxybenzyl)glycine is prepared by reacting glycine with 2,4-dimethoxybenzaldehyde in the presence of sodium hydroxide, reducing with palladium-on-carbon in methanol and subsequently neutralizing with 2N hydrochloric acid. The aqueous solution obtained is concentrated. 18.6 g of the mixture of N-(2,4-dimethoxybenzyl)glycine and sodium chloride obtained are stirred at 80° and 90°, in each case for 1 hour, together with 60 ml of N,N-dimethylformamide and 10 g (50.6 mmol) of 6-chloroisatoic anhydride. The reaction mixture is evaporated and the residue is heated at 135°-140° for 5 hours in a high vacuum. The crystalline product is boiled in 90 ml of N,N-dimethylformamide, whereupon the mixture is poured into 400 ml of hot water. The mixture is left to cool to room temperature while stirring, then cooled to about 0° in an ice-bath, the product is filtered off under suction, rinsed with water and the material obtained is dissolved in 20 ml of hot N,N-dimethylformamide. After the addition of 150 ml of ethyl acetate the mixture is left to stand in an ice-bath for 1 hour, the product is filtered off under suction, rinsed with cold ethyl acetate and dried at 80° in vacuo. There is obtained 6-chloro-4-(2,4-dimethoxybenzyl)-3,4-dihydro-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 230°-231°.
Workup
- customThe aqueous solution obtained
- concentrationis concentrated
Sources & evidence
- ORD record
- ord-c1d2453170b04a15bc696d28df96243f
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775671
Reaction notes
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