HCID 20215189, compound → HCID 20215193, compound

HRID 1905761Notes

Reaction equation

HRID 1905761 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-])=O)[CH:8]=[C:9]([CH3:15])[C:10]=1[O:11][CH2:12][C:13]#[N:14])(=[O:4])[CH2:2][CH3:3]>C(O)(=O)C.[Fe]>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([CH3:15])[C:10]=1[O:11][CH2:12][C:13]#[N:14])[NH2:16])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 20215189HCID 20215189, compound

Product 1

HCID 20215193HCID 20215193, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

3-Propionyl-4-cyanomethoxy-5-methylnitrobenzene (X =CH3 ; ##STR16## R1 =-CH2C≡N) (4.96 g) in acetic acid (60 ml) was dropwise added to an aqueous solution (300 ml) containing acetic acid (15 ml) and iron (20 g). The resulting mixture was kept at 40° C. for 4 hours with vigorous stirring. The solid was removed by filtration, and the filtrate was extracted with dichloromethane. The extract was washed with an aqueous solution of potassium carbonate and water, dried over magnesium sulfate and concentrated under reduced pressure to give 3-propionyl-4-cyanomethoxy-5-methylaniline (3.88 g) in a yield of 88.8%. NMR δ (CDCl3): 1.18 (t, 3H), 2.30 (s, H), 2.85 (q, 2H), 4.61 (s, 2H), 6.68 (s, 2H).

Workup

  1. customThe solid was removed by filtration
  2. extractionthe filtrate was extracted with dichloromethane
  3. washThe extract was washed with an aqueous solution of potassium carbonate and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-949054a80d0e4bf1af8276aa13a19fd1
Source dataset
uspto-grants-1987_03
Patent number
US04647584

Reaction notes

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