1,3,3-Trimethyl-2-methyleneindoline → HCID 22336199, compound

HRID 1605274Notes

Reaction equation

HRID 1605274 reaction equation
[OH:1][C:2]1C=CC2[C:4](=CC=C([N+]([O-])=O)C=2)[C:3]=1C=O.C[N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](C)(C)[C:19]1=[CH2:29]>C(O)C>[O:1]1[CH:2]=[CH:3][CH:4]=[CH:29][C:19]21[CH2:20][C:21]1[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:18]2

Participants

4

Reactant 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 35679732-hydroxy-6-nitronaphthalene-1-carbaldehyde

Product 1

HCID 22336199HCID 22336199, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution is prepared of 2.17 g. (0.0295 mole) of 2-hydroxy-6-nitro-1-naphthaldehyde in 80 cm3 of hot ethanol, to this is added 1.73 g. (0.0295 mole) of 1,3,3-trimethyl-2-methyleneindoline and the mixture is heated for two hours at boiling temperature under reflux. The mixture is then cooled to 0° C. and a precipitate of indolinespiropyran is obtained. This is filtered and dried. The composition has a melting point of 234° C. The product is recrystallized twice from benzene and the melting point is increased to 240°-241° C. The purified product weight is 1.34 g. which represents a recovery of 36%.

Workup

  1. customA solution is prepared of 2.17 g
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-29c32fe3388d4e0e933295cb379e088c
Source dataset
uspto-grants-1976_04
Patent number
US03950356

Reaction notes

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