Succinic anhydride → HCID 67088928, compound

HRID 1910378Notes

Reaction equation

HRID 1910378 reaction equation
[CH3:1][C:2]1([CH3:26])[C:10]2([O:15][C:14]3[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=3[CH:12]=[CH:11]2)[N:9]([CH2:23][CH2:24][OH:25])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(N(CC)CC)C.[C:34]1(=[O:40])[O:39][C:37](=[O:38])[CH2:36][CH2:35]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1([CH3:26])[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:9]([CH2:23][CH2:24][O:25][C:34](=[O:40])[CH2:35][CH2:36][C:37]([OH:39])=[O:38])[C:10]21[CH:11]=[CH:12][C:13]1[C:14](=[CH:16][CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[O:15]2

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 31048582-(3',3'-Dimethyl-6-nitrospiro[1-benzopyran-2,2'-indol]-1'(3'H)-yl)ethan-1-ol

Product 1

HCID 67088928HCID 67088928, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

About 2 g of 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6′-nitrobenzopyrylospiran (TCI America), about 0.44 ml of triethylamine, and about 0.69 g of 4-(dimethylamino)pyridine were dissolved in about 30 ml of dichloromethane. After addition of about 0.59 g of succinic anhydride, the solution was stirred under Ar at room temperature for about 19 hours. The mixture was washed with 5% aqueous hydrochloric acid, aqueous sodium bicarbonate, and water, then dried over magnesium sulfate. After the solvent was distilled off, the concentrated solution was added dropwise to hexane under stirring. The resulting solid was collected by filtration to yield 4-(2-(3′,3′-dimethyl-6-nitrospiro[chromene-2,2′-indoline]-1′-yl)ethoxy)-4-oxobutanoic acid.

Workup

  1. washThe mixture was washed with 5% aqueous hydrochloric acid, aqueous sodium bicarbonate, and water
  2. dry with materialdried over magnesium sulfate
  3. distillationAfter the solvent was distilled off
  4. additionthe concentrated solution was added dropwise to hexane
  5. stirringunder stirring
  6. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-00e6d514360346e691e004786f7658fe
Source dataset
uspto-grants-2013_12
Patent number
US08603944B2

Reaction notes

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