Diethyl Ether → 4-[(2-Methyl-hydrazino)-methyl]-benzoic acid (1,1-dimethyl-2-hydroxy-ethyl)-amide oxalate

HRID 1579710Notes

Reaction equation

HRID 1579710 reaction equation
C[N:2]([C:24](OCC1C=CC=CC=1)=O)[N:3]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)[C:4]([O:6]CC1C=CC=CC=1)=[O:5].CCOCC.[NH2:39][C:40]([CH3:44])([CH3:43])[CH2:41][OH:42].[C:45](=[O:48])([O-:47])[O-].[Na+].[Na+]>O>[C:4]([OH:6])(=[O:5])[C:45]([OH:47])=[O:48].[CH3:43][C:40]([NH:39][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:3][NH:2][CH3:24])=[CH:23][CH:22]=1)([CH3:44])[CH2:41][OH:42]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 118072-Amino-2-methyl-1-propanolHCID 215690594-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoyl chloride

Product 1

HCID 1317098894-[(2-Methyl-hydrazino)-methyl]-benzoic acid (1,1-dimethyl-2-hydroxy-ethyl)-amide oxalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.8 g. of 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)methyl]-benzoyl chloride were dissolved in 50 ml. of dry ether and, wherein 30 minutes within stirring, added dropwise to a solution of 3.3 g. of 2-amino-2-methyl-1-propanol and 3.6 g. of anhydrous sodium carbonate in 50 ml. of water. The solution was stirred overnight at 0°, the mixture diluted with 100 ml. of water and extracted 3 times with 100 ml. of methylene chloride each time. The united methylene chloride extracts were freed off the solvent in vacuo and the residue dissolved in 200 ml. of methanol, whereupon it was hydrogenated in the presence of 2 g. of 5% palladium-carbon. The colorless glacial material was transformed according to Example 20 into its oxalic acid salt. The crystalline crude material was recrystallized from methanol/acetonitrile, yielding 4-[(2-methyl-hydrazino)-methyl]-benzoic acid (1,1-dimethyl-2-hydroxy-ethyl)-amide oxalate as colorless platelets melting at 160°-162° (dec.).

Workup

  1. additionadded dropwise to a solution of 3.3 g
  2. additionthe mixture diluted with 100 ml
  3. extractionof water and extracted 3 times with 100 ml
  4. dissolutionthe residue dissolved in 200 ml
  5. customThe crystalline crude material was recrystallized from methanol/acetonitrile

Sources & evidence

ORD record
ord-95b127a778d040f38f29adf1fc1f5dc0
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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