Methanol → HCID 66759374, compound

HRID 1402773Notes

Reaction equation

HRID 1402773 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:22][C:21](=[O:23])[O:20][C:18](=[O:19])[CH2:17]2)=[CH:12][CH:11]=1.CO>O1CCOCC1>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][C:21](=[O:23])[CH2:22][CH:16]([C:13]1[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=1)[CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 7243O-PhenylenediamineHCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

Product 1

HCID 66759374HCID 66759374, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The solution of commercial 1,2-phenylenediamine (1.08 g) and 3-(4-chlorophenyl)glutaric anhydride (2.25 g) in 1,4-dioxane (7 ml) was stirred at rt for 10 min. A voluminous precipitate is formed which is kept at rt for further 50 min. The thick slurry is heated to reflux with methanol, cooled to rt, isolated by suction filtration, and washed with methanol. After drying in vacuo N-(2-aminophenyl)-3-(4-chlorophenyl)glutaramic acid (2.1 g) is obtained as off-white solid.

Workup

  1. customA voluminous precipitate is formed which
  2. temperatureThe thick slurry is heated
  3. customisolated by suction filtration
  4. washwashed with methanol
  5. dry with materialAfter drying in vacuo N-(2-aminophenyl)-3-(4-chlorophenyl)glutaramic acid (2.1 g)
  6. customis obtained as off-white solid

Sources & evidence

ORD record
ord-d4dd595954804945991d5798438125cd
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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