Hydrochloric Acid → HCID 5115807, compound

HRID 992741Notes

Reaction equation

HRID 992741 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:14]#N)[C:10]([O:12][CH3:13])=[O:11])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1.[CH3:19][OH:20].C1(C)C=CC=CC=1.Cl.[OH2:29]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:14]([O:20][CH3:19])=[O:29])[C:10]([O:12][CH3:13])=[O:11])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 1140TolueneHCID 57193434HCID 57193434, compound

Product 1

HCID 5115807HCID 5115807, compoundYield 86%

Procedure

A 80 mL Fischer-Porter® bottle (Fischer-Porter Co., Warminster, Pa.) equipped with a gas pressure head and a magnetic stirring bar was charged with methyl 4-methoxy-2-nitrophenyl-α-cyano-acetate from Example 10 (5.0 g, 0.020 mol), methanol (3 mL), toluene (50 mL), sealed, and then charged with HCl gas (55 psig). After stirring for 4 hours at ambient temperature, the apparatus was vented and water (50 mL) was added. The toluene layer was separated and evaporated to dryness under vacuum to afford 5.1 g of dimethyl 4-methoxy-2-nitrophenylmalonate as a tan colored solid (1H-NMR). By HPLC area % analysis (254 nm), the solid was 95% dimethyl 4-methoxy-2-nitrophenylmalonate and 5% methyl 4-methoxy-2-nitrophenyl-α-carbamido-acetate. Isolated yield: 86% on methyl 4-methoxy-2-nitrophenyl-α-cyanoacetate.

Workup

  1. customA 80 mL Fischer-Porter® bottle (Fischer-Porter Co., Warminster, Pa.) equipped with a gas pressure head and a magnetic stirring bar
  2. customsealed
  3. customThe toluene layer was separated
  4. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-6d541157045c4c77a4c96f25fde1ff34
Source dataset
uspto-grants-2002_10
Patent number
US06469181B1

Reaction notes

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