Hydrochloric Acid → HCID 19870549, compound

HRID 330161Notes

Reaction equation

HRID 330161 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([O:14]C)=[O:13])[CH:8]=2)[C:3](/[CH:16]=[CH:17]/[C:18]([O:20]C)=[O:19])=[CH:2]1.O.[OH-].[Li+].CO.Cl>O.O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])[CH:8]=2)[C:3](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 19870610HCID 19870610, compound

Product 1

HCID 19870549HCID 19870549, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of dimethyl E,E-indole-3,6-diacrylate (1.1 g), lithium hydroxide monohydrate (1.29 g), methanol (25 ml), tetrahydrofuran (10 ml) and water (5 ml) was stirred and heated at 55°-60° for 7 hr under an atmosphere of nitrogen. The cooled mixture was diluted with water (30 ml) and acidified to pH 4 with 6M hydrochloride acid. The yellow precipitate was isolated by filtration, washed with water and dried under vacuum to give E,E-indole-3,6-diacrylic acid (0.87 g, 88%) as a solid; mp >360°; partial NMR (250 MHz, DMSO-d6): 6.33(d, J=16.0 Hz, 1H, olefinic H), 6.49(d, J=16.0 Hz, 1H, olefinic H), 11.94(br s, 1H, NH), 12.10(br s, 1H, COOH).

Workup

  1. temperatureheated at 55°-60° for 7 hr under an atmosphere of nitrogen
  2. customThe yellow precipitate was isolated by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-dee398546d8a48c5beb85f92a9847970
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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