Hydrochloric Acid → HCID 19698376, compound

HRID 862574Notes

Reaction equation

HRID 862574 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)=[CH:6][C:5]=1[CH:22](C(OCC)=O)[C:23]([O:25][CH2:26]C)=[O:24])([O-:3])=[O:2].[ClH:33]>O1CCOCC1>[ClH:33].[NH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53942467HCID 53942467, compound

Product 1

HCID 19698376HCID 19698376, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of diethyl 2-nitro-5-phthalimidomethylphenylmalonate in a mixture of concentrated hydrochloric acid (150 mL) and 1,4-dioxane (150 mL) was heated at 120° C. for 24 h. The solvents was removed in vacuo and the residual solid was dissolved in methanol (100 mL). To the solution was added thionyl chloride (11.8 g) dropwise at 0° C. The mixture was stirred for 2 h at 40° C. and the solvent and the excess reagent was removed in vacuo. The residue was washed with diethyl ether and dried to give 6.5 g of the title compound (quant).

Workup

  1. customThe solvents was removed in vacuo
  2. dissolutionthe residual solid was dissolved in methanol (100 mL)
  3. additionTo the solution was added thionyl chloride (11.8 g) dropwise at 0° C
  4. customthe solvent and the excess reagent was removed in vacuo
  5. washThe residue was washed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-5414ba1a69eb438087e12fe62f71ba4c
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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