Potassium Hydroxide → 1(3H)-Isobenzofuranone, 3-[2,4-bis(dimethylamino)phenyl]-6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-

HRID 569673Notes

Reaction equation

HRID 569673 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:30]=[C:29]([N:31]([CH3:33])[CH3:32])[CH:28]=[CH:27][C:4]=1[CH:5]([C:15]1[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[OH-].[K+].C(=O)(O)[O-].[Na+]>O>[CH3:34][N:2]([CH3:1])[C:3]1[CH:30]=[C:29]([N:31]([CH3:33])[CH3:32])[CH:28]=[CH:27][C:4]=1[C:5]1([C:6]2[CH:7]=[CH:8][C:9]([N:12]([CH3:13])[CH3:14])=[CH:10][CH:11]=2)[C:15]2[C:16](=[CH:20][C:21]([N:24]([CH3:25])[CH3:26])=[CH:22][CH:23]=2)[C:17](=[O:19])[O:18]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 112438HCID 112438, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 1036931(3H)-Isobenzofuranone, 3-[2,4-bis(dimethylamino)phenyl]-6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-Yield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 29.78 g of 2-[2,4,4'-tris(dimethylamino)benzhydryl]-5-dimethylaminobenzoic acid prepared as described in part B above, 450.0 g of water and 16.2 g of flake potassium hydroxide was prepared and the pH adjusted to 10.0 by the gradual addition of sodium bicarbonate. The solution was then heated at approximately 75° C. under an atmosphere of oxygen at 60-65 psi for approximately six hours in an agitated stainless steel autoclave. The solid which separated was collected by filtration at ambient temperature, washed with water until alkali free when tested with Brilliant Yellow test paper and dried. The dried solid was slurried with hexane at room temperature, filtered and dried to obtain 23.6 g of 3-(2,4-bis[dimethylamino]phenyl)-3-(4-dimethylaminophenyl)-6-dimethylaminophthalide (Formula I: R=CH3 ; X=H; Y=4-(CH3)2NC6H4 ; Z=2,4-[(CH3)2N]2C6H3) a pale blue-colored solid melting at 171°-172° C.

Workup

  1. customwas prepared
  2. customThe solid which separated
  3. filtrationwas collected by filtration at ambient temperature
  4. washwashed with water until alkali free when
  5. customdried
  6. customwas slurried with hexane at room temperature
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-3139c3b61c624859a062e533a1578b93
Source dataset
uspto-grants-1988_03
Patent number
US04732991

Reaction notes

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