Hydrochloric Acid → HCID 178494654, compound

HRID 380410Notes

Reaction equation

HRID 380410 reaction equation
[NH:1]=[C:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:10]([O:12][CH3:13])=[O:11])[CH2:3][O:4][CH3:5].Cl.Cl[O-].[Na+]>CO>[CH3:18][O:17][C:16]1[C:7]2[N:6]=[C:2]([CH2:3][O:4][CH3:5])[NH:1][C:8]=2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665760Sodium Hypochlorite2×HCID 178496045HCID 178496045, compound

Product 1

HCID 178494654HCID 178494654, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-(1-imino-2-methoxy-ethylamino)-4-methoxybenzoate [15.7 g, Reference Example 4(a)] in methanol (150 ml) was treated with 1M hydrochloric acid (62.6 ml) then with sodium hypochlorite solution (32.3 ml, 13%). Further aliquots of sodium hypochlorite solution were added until all the starting material was consumed. The solution containing methyl 3-(1-chloroimino-2-methoxy-ethylamino)-4-methoxybenzoate was treated with a saturated solution of sodium carbonate (8.62 g) in water. The mixture was then refluxed for 1 hour, then cooled to room temperature, then diluted with water and then extracted with chloroform. The chloroform extract was washed with brine, dried over magnesium sulphate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:1, v/v) then with a mixture of ethyl acetate and hexane (6:1, v/v) to give the title compound (13.0 g) as a solid. M+250. NMR (CDCl3): δ 3.48(s,3H), 3.98(s,3H), 4.10(s,3 H), 4.78(s,2H), 6.70(d,J=8 Hz,1H), 7.87(d,J=8 Hz,1H).

Workup

  1. customwas consumed
  2. additionThe solution containing methyl 3-(1-chloroimino-2-methoxy-ethylamino)-4-methoxybenzoate
  3. additionwas treated with a saturated solution of sodium carbonate (8.62 g) in water
  4. temperatureThe mixture was then refluxed for 1 hour
  5. additiondiluted with water
  6. extractionextracted with chloroform
  7. extractionThe chloroform extract
  8. washwas washed with brine
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:1
  12. additionv/v) then with a mixture of ethyl acetate and hexane (6:1

Sources & evidence

ORD record
ord-e4b3ad6059674438a583fe6e90986812
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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