Toluene → 2-[5-(Benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetal

HRID 2293724Notes

Reaction equation

HRID 2293724 reaction equation
Cl[C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:19][O:20][CH:21]([O:25][CH3:26])[CH:22]([NH2:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CS(C)=O>[CH3:19][O:20][CH:21]([O:25][CH3:26])[CH:22]([NH:24][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH3:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 936582,2-Dimethoxy-1-methylethylamineHCID 8198614-(Benzyloxy)-2-chloro-1-nitrobenzene

Product 1

HCID 190831162-[5-(Benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetal

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of benzyl 3-chloro-4-nitrophenyl ether (48.2 g, 0.183 mole), 2-aminopropionaldehyde dimethyl acetal (65.3 g, 0.55mole), potassium carbonate (101 g, 0.73 mole) and toluene in dry dimethyl sulfoxide, under nitrogen, is stirred at 99°-105° C. for 20 hours, cooled to room temperature and filtered. The filter cake is washed with ether. The combined filtrates are mixed with ice water. The phases are separated and the aqueous phase is extracted with ether. The ether extracts are combined with the organic phase. The combined organic phase is washed with six portions of water, dried (Na2SO4) and concentrated in vacuo to give an oil residue which is crystallized in methanol to afford the title product as a yellow solid, 39.6 g (64.5%). A sample is recrystallized from methanol to afford a yellow solid, mp 57°-62° C., identified by elemental and NMR analyses.

Workup

  1. filtrationfiltered
  2. washThe filter cake is washed with ether
  3. additionThe combined filtrates are mixed with ice water
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with ether
  6. washThe combined organic phase is washed with six portions of water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto give an oil residue which
  10. customis crystallized in methanol

Sources & evidence

ORD record
ord-b0a2f470195448cd9e2e69823de6a109
Source dataset
uspto-grants-1997_11
Patent number
US05686617

Reaction notes

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