4-methoxy-2-methyl-N-phenylaniline → 3-(4-Dibutylamino-2-hydroxyphenyl)-3-(5-anilino-2-methoxyphenyl)phthalide

HRID 1195249Notes

Reaction equation

HRID 1195249 reaction equation
[CH2:1]([N:5]([CH2:24][CH2:25][CH2:26][CH3:27])[C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=[O:11])=[C:8]([OH:23])[CH:7]=1)[CH2:2][CH2:3][CH3:4].C[C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1[NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>S(=O)(=O)(O)O>[CH2:24]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:22]=[CH:21][C:9]([C:10]2([C:34]3[CH:29]=[C:30]([NH:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:31]=[CH:32][C:33]=3[O:35][CH3:36])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14](=[O:15])[O:11]2)=[C:8]([OH:23])[CH:7]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 1624614-methoxy-2-methyl-N-phenylanilineHCID 19108252-[4-(Dibutylamino)-2-hydroxybenzoyl]benzoic acid

Product 1

HCID 198190353-(4-Dibutylamino-2-hydroxyphenyl)-3-(5-anilino-2-methoxyphenyl)phthalide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

There is described in Japanese Patent Laid-open No. 60-202155 that a known conventional method provides a low melting type 3-dibutylamino-6-methyl-7-anilinofluoran. The conventional method is as follows. 2-(4-Dibutylamino-2-hydroxybenzoyl)benzoic acid and 4-methoxy-2-methyldiphenylamine are dissolved in concentrated sulfuric acid, and the reaction is carried out at 0°-5° C. for 20 hours. After the reaction, the reaction mixture is poured into ice water, whereupon precipitates are formed. The precipitates are collected by filtration and washed with water to provide a cake of 3-(4-dibutylamino-2-hydroxyphenyl)-3-(5-anilino-2-methoxyphenyl)phthalide. The cake is added to a mixture of toluene and water, and then the mixture is neutralized with a 28% by weight aqueous solution of sodium hydroxide. A further amount of sodium hydroxide is added and then the mixture is stirred at a refluxing temperature for three hours. After the reaction, the mixture is left standing, and a toluene layer is separated and concentrated at 70° C. until a syrup is obtained. Methanol is added to the syrup so that 3-dibutylamino-6-methyl-7-anilinofluoran crystalizes out. According to the reference, the obtained compound has a melting point of 148°-152° C.

Workup

  1. customAfter the reaction
  2. customwhereupon precipitates
  3. customare formed
  4. filtrationThe precipitates are collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-b23ae8e6d49f4522979bc4ac9ba32fe4
Source dataset
uspto-grants-1992_05
Patent number
US05110952

Reaction notes

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