Hydrochloric Acid → 3-((1-Ethylpropyl)amino)-6-methyl-2,4-dinitrobenzyl alcohol

HRID 1577485Notes

Reaction equation

HRID 1577485 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[C:8]([NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:7]=1[N+:22]([O-:24])=[O:23])(=O)C.Cl.O>CO>[CH2:18]([CH:17]([NH:16][C:8]1[C:7]([N+:22]([O-:24])=[O:23])=[C:6]([C:11]([CH3:12])=[CH:10][C:9]=1[N+:13]([O-:15])=[O:14])[CH2:5][OH:4])[CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 129407633-[(1-Ethylpropyl)amino]-6-methyl-2,4-dinitrobenzyl acetate

Product 1

HCID 1566883-((1-Ethylpropyl)amino)-6-methyl-2,4-dinitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sample of 3-[(1-ethylpropyl)amino]-6-methyl-2,4-dinitrobenzyl acetate (23.1 g; 0.068 mol) is added to a mixture of concentrated hydrochloric acid (30 ml), water (40 ml) and methanol (320 ml). The reaction mixture is refluxed for 4 hours, cooled down and concentrated in vacuo. It is then diluted with water, extracted with ether, and the ether layer dried. The ether is removed in vacuo to leave a red oil, which readily solidifies to a yellow-orange solid (19.9 g; 98.5%). A similarly prepared and purified sample has a melting point of 51°-54° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. temperaturecooled down
  3. concentrationconcentrated in vacuo
  4. additionIt is then diluted with water
  5. extractionextracted with ether
  6. dry with materialthe ether layer dried
  7. customThe ether is removed in vacuo
  8. customto leave a red oil, which
  9. customA similarly prepared
  10. custompurified sample

Sources & evidence

ORD record
ord-5d83b8539f184fda89fc8be8dd7b8a25
Source dataset
uspto-grants-1981_09
Patent number
US04288385

Reaction notes

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