Ethanol → 1,6-di(4-methoxyphenyl)-4,5-dihydro-2H-3-oxa-4-azabenz-[e]-as-indacene

HRID 1155984Notes

Reaction equation

HRID 1155984 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19](O)[C:20](O)=O)=[CH:17][CH:16]=1.Cl[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1Cl.[N+]([C:37]1[CH:42]=CC=CC=1)([O-])=O.[CH2:43]([OH:45])C>>[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]2[CH2:20][O:12][C:3]3[C:4]=2[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]2[C:2]=3[NH:1][CH2:42][C:37]=2[C:27]2[CH:32]=[CH:31][C:30]([O:45][CH3:43])=[CH:29][CH:28]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 72391,2-DichlorobenzeneHCID 7416NitrobenzeneHCID 794493-Amino-2-naphtholHCID 1120564-Methoxymandelic acid

Product 1

HCID 205363231,6-di(4-methoxyphenyl)-4,5-dihydro-2H-3-oxa-4-azabenz-[e]-as-indacene

Procedure

A mixture of 1.6 parts of 3-amino-2-naphthol, 5.46 parts of 4-methoxymandelic acid and 25 parts of 1,2-dichlorobenzene is heated under reflux for 20 hours when 2.5 parts of nitrobenzene are added and heating is continued for a further 11/2 hours. After cooling, the mixture is diluted with 50 parts of ethanol. The highly crystalline product is isolated by filtration to give 1,6-di(4-methoxyphenyl)-4,5-dihydro-2H-3-oxa-4-azabenz-[e]-as-indacene having m.p. 340° C. The dyestuff dissolves in chloroform to give an orange solution having λmax 464 nm, εmax 35,000. When applied to aromatic polyester textile materials from aqueous dispersion by batchwise dyeing orange shades are obtained.

Workup

  1. temperatureis heated
  2. additionare added
  3. temperatureheating
  4. custom2 hours
  5. temperatureAfter cooling
  6. customThe highly crystalline product is isolated by filtration

Sources & evidence

ORD record
ord-15802e81489242b1a53b4e6d7f7e28c9
Source dataset
uspto-grants-1982_06
Patent number
US04333877

Reaction notes

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