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Aniline → HCID 10948950, compound

HRID 1957792
Notes
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Reaction equation

HRID 1957792 reaction equation
[OH:1][C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]([OH:17])=O)[CH:8]=2)[CH:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.P(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1.O>[OH:1][C:2]1[C:11]([C:12]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:17])[CH:8]=2)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 24387Phosphorus trichlorideHCID 98160552-Hydroxynaphthalen-3,6-dicarboxylic acid

Product 1

HCID 10948950HCID 10948950, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

2-Hydroxy-3,6-dihydroxycarbonylnaphthalene (4.64 g) and aniline (4.10 g) were dispersed in xylene (92.8 g), followed by heating to 90° C. Phosphorous trichloride (2.4 g) was added dropwise at 90° to 100° C., and then the mixture was reacted at 140° C. for 3 hours. After the completion of the reaction, water (92.8 g) was added and the reaction solution was neutralized with sodium carbonate at 90° C. The solution was filtered at room temperature and washed in turn with xylene (46.4 g) and water (46.4 g). The resultant crystal was subjected to reflux washing using acetone (80 g) and then filtered. This operation was repeated three times, followed by drying to obtain 3.5 g of 2-hydroxy-3,6-diphenylaminocarbonylnaphthalene as a white powdered crystal (melting point: 314°-317° C.).

Workup

  1. customthe mixture was reacted at 140° C. for 3 hours
  2. additionwas added
  3. filtrationThe solution was filtered at room temperature
  4. washwashed in turn with xylene (46.4 g) and water (46.4 g)
  5. temperatureto reflux
  6. washwashing
  7. filtrationfiltered
  8. customby drying

Sources & evidence

ORD record
ord-c060c24a45294806b8b41fc4f7719a0e
Source dataset
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05786523

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes