Toluene → HCID 14369974, compound

HRID 1381509Notes

Reaction equation

HRID 1381509 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])([O-])=O.[S:15]([O-:19])([O-])(=O)=[O:16].[Mg+2].[H][H].[C:23]1(C)C=CC=CC=1>[Pd]>[CH3:23][S:15]([NH:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:19])=[O:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 520464Methyl 2-(2-nitrophenyl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 14369974HCID 14369974, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of methyl 2-nitrophenylacetate, (6.04 kg) in toluene (100 l) is added anhydrous magnesium sulfate (2.00 kg) and then 5% palladium-on-charcoal (125 g). The mixture is then stirred and hydrogenated, keeping the temperature below 40° by regulation of the stirring rate and input of hydrogen gas. After the addition is complete, the mixture is filtered. The filtrate containing methyl 2-aminophenylacetate is cooled to -20° and triethylamine (3.75 kg) is added all at once with stirring. This is followed by the slow addition of a solution of methanesulfonyl chloride (3.91 kg) in toluene (4.5L), keeping the temperature between -2° and 5°. After stirring at -2° for 1 hour, the mixture is filtered and washed with toluene (10 l). The filter cake is then slurried with water (90 l) for 90 minutes, filtered, and washed with water (45 l) and methanol (8 l). The solid is dried at 50° in vacuo overnight to yield methyl 2-(methylsulfonylamino)phenylacetate, mp 73°-75°.

Workup

  1. customthe temperature below 40°
  2. additionAfter the addition
  3. filtrationthe mixture is filtered
  4. additionThe filtrate containing methyl 2-aminophenylacetate
  5. temperatureis cooled to -20°
  6. additiontriethylamine (3.75 kg) is added all at once
  7. stirringwith stirring
  8. additionThis is followed by the slow addition of a solution of methanesulfonyl chloride (3.91 kg) in toluene (4.5L)
  9. customthe temperature between -2° and 5°
  10. stirringAfter stirring at -2° for 1 hour
  11. filtrationthe mixture is filtered
  12. washwashed with toluene (10 l)
  13. filtrationfiltered
  14. washwashed with water (45 l) and methanol (8 l)
  15. customThe solid is dried at 50° in vacuo overnight

Sources & evidence

ORD record
ord-f752fa5a77004f7c8543f9459a3832ca
Source dataset
uspto-grants-1989_02
Patent number
US04803197

Reaction notes

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