HCID 59726037, compound → HCID 59726039, compound

HRID 336432Notes

Reaction equation

HRID 336432 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:13]([O-])=O)[C:3]=1[O:16][CH3:17]>C(O)(=O)C.[Fe]>[NH2:13][C:4]1[C:3]([O:16][CH3:17])=[C:2]([Cl:1])[CH:11]=[C:10]([Cl:12])[C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 59726037HCID 59726037, compound

Product 1

HCID 59726039HCID 59726039, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

Iron powder (18.2 g, 330 mmol) was added to a solution of methyl ester 2-2 (13.3 g, 480 mmol) in glacial acetic acid (120 mL). The mixture was stirred at 55° C. for 1.5 h and then filtered hot through celite, washing with ethyl acetate. The filtrate was concentrated then ethyl acetate and sat. aq. NaCO3 were added. The organic layer was isolated, washed with H2O, dried over K2CO3 and concentrated to give 2-3 as an off-white solid (11.6 g, 97% yield). 1H NMR (CDCl3, 400 MHz) δ 3.79 (s, 3H), 3.89 (s, 3H), 6.71 (s, 1H).

Workup

  1. filtrationfiltered hot through celite
  2. washwashing with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. additionethyl acetate and sat. aq. NaCO3 were added
  5. customThe organic layer was isolated
  6. washwashed with H2O
  7. dry with materialdried over K2CO3
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c1c4504b7a946f8914eb2ba5798afe4
Source dataset
uspto-grants-2014_11
Patent number
US08889695B2

Reaction notes

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