Methane → HCID 13853487, compound

HRID 542612Notes

Reaction equation

HRID 542612 reaction equation
[C:1]([C:5]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[C:14]([Cl:22])[C:6]=1[N:7](C(=O)C)C(=O)C)([O:3]C)=[O:2].[OH-].[Na+].C>C(O)(=O)C>[Cl:22][C:14]1[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:5]([C:1]([OH:3])=[O:2])[C:6]=1[NH2:7]

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 13853486HCID 13853486, compound

Product 1

HCID 13853487HCID 13853487, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2,4 g (97.3 mmol) of 2-carbomethoxy-6-chloro-N,N-diacetyl-3,4-dimethoxyaniline and 20 mL of 2N sodium hydroxide was refluxed 3.5 hours. The solution was treated with Darco and neutralized with 5 mL of glacial acetic acid. Upon cooling, the product crystallized and was collected by filtration to yield 0.6 g (36%) of a fluffy yellow solid, mp 140°-142° C. NMR (CDCl3) δ 3.82 (s, 3H, OCH3), 4.03 (s, 3H, OCH3). 7.15 (s, 1H, ArH).

Workup

  1. temperaturewas refluxed 3.5 hours
  2. temperatureUpon cooling
  3. customthe product crystallized
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b4f5169d36734ae195a5bb46f28f7876
Source dataset
uspto-grants-1987_04
Patent number
US04658054

Reaction notes

Loading…