1,1-Dimethoxyethyl(dimethyl)amine → 1-(4'-Hydroxymethyl-4,6-dinitro-biphenyl-3-yl)-propan-2-one

HRID 1773536Notes

Reaction equation

HRID 1773536 reaction equation
[CH3:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)[CH:7]=1.C[O:23][C:24](OC)(N(C)C)[CH3:25]>C(OCC)(=O)C>[OH:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][C:3]([N+:19]([O-:21])=[O:20])=[C:2]([CH2:1][C:24](=[O:23])[CH3:25])[CH:7]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 58056286(5'-Methyl-2',4'-dinitro-biphenyl-4-yl)-methanol

Product 1

HCID 580561251-(4'-Hydroxymethyl-4,6-dinitro-biphenyl-3-yl)-propan-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5′-methyl-2′,4′-dinitro-biphenyl-4-yl)-methanol (0.6 g) in N,N-dimethylacetamide dimethylacetal (5 mL) was heated at 100° C. for 2 hour. The reaction mixture was then cooled, diluted with ethyl acetate, washed with a diluted aqueous solution of hydrochloric acid, water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (acetone/DCM, 3/97) to afford 1-(4′-hydroxymethyl-4,6-dinitro-biphenyl-3-yl)-propan-2-one.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with a diluted aqueous solution of hydrochloric acid, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (acetone/DCM, 3/97)

Sources & evidence

ORD record
ord-3380bff9712444209439b3c29374baba
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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