Hydrochloric Acid → HCID 14882675, compound

HRID 330153Notes

Reaction equation

HRID 330153 reaction equation
O.[OH-].[Li+].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10](/[CH:13]=[CH:14]/[C:15]([O:17]C)=[O:16])[CH:11]=2)[CH:6]=[CH:5]1.Cl>CO.O1CCCC1.O>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])[CH:11]=2)[CH:6]=[CH:5]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 13707694HCID 13707694, compound

Product 1

HCID 14882675HCID 14882675, compoundYield 97.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (4.6 g) was added to a stirred solution of methyl E-indole-6-acrylate (5.5 g) in methanol (100 ml), tetrahydrofuran (10 ml), and water (10 ml) under an atmosphere of nitrogen; and the mixture was heated at 50° for 5 hr. The cooled mixture was diluted with water (100 ml) and acidified to pH 4 with 6M hydrochloric acid. The precipitate which formed was isolated by filtration, washed twice with water, and dried to give E-indole-6-acrylic acid (5 g, 97%) as a yellow powder; mp 215°-217°; partial NMR (250 MHz, DMSO-d6): 6.42(d, J=15.9 Hz, 1H, olefinic H), 6.47(m, 1H, H3 -indole), 7.70(d, J=15.9 Hz, 1H, olefinic H), 11.35(br s, 1H, NH), 12.18(br s, 1H, COOH).

Workup

  1. temperatureand the mixture was heated at 50° for 5 hr
  2. customThe precipitate which formed
  3. customwas isolated by filtration
  4. washwashed twice with water
  5. customdried

Sources & evidence

ORD record
ord-598b2b3e0df84a0e80fb0e6537b0cff4
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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