Hydrochloric Acid → HCID 19698376, compound

HRID 1439896Notes

Reaction equation

HRID 1439896 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) at 0° C. The mixture was stirred for 2 h at 40° C. and the solvent and the excess reagent were removed in vacuo. The residue was washed with diethyl ether and dried to give 6.5 g of the title compound (quant): 1H NMR (CD3OD) δ8.18 (d, 1H, J=8.6 Hz), 7.63 (dd, 1H, J=8.6, 1.6 Hz), 7.56 (d, 1H, J=1.6 Hz), 4.23 (s, 2H), 4.09 (s, 2H), 3.69 (s, 3H).

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) at 0° C
  4. customthe solvent and the excess reagent were removed in vacuo
  5. washThe residue was washed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-23d61bf9301d43fca9624e0c3fa045e5
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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