Hydrochloric Acid → HCID 70215201, compound

HRID 2268223Notes

Reaction equation

HRID 2268223 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]([O:27]C)=[O:26])[CH:20]=[CH:21][CH:22]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2.C1COCC1.[OH-].[Li+].Cl>O>[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 70213304HCID 70213304, compound

Product 1

HCID 70215201HCID 70215201, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.9 g (7.4 mmol) of methyl 3-{3-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbonyl)-amino]phenyl}acrylate obtained in Example 18, 50 ml of THF and 3.1 g (74 mmol) of lithium hydroxide are introduced into a round-bottomed flask. The reaction medium is refluxed for 24 h ours and then poured into water, acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is triturated from heptane, filtered off and dried. 2.8 g (100%) of 3-{3-[(5,5,8,8- tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbonyl) amino]phenyl}acrylic acid, with a melting point of 215-6° C., are collected.

Workup

  1. temperatureThe reaction medium is refluxed for 24 h ours
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is separated out after settling
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis triturated from heptane
  9. filtrationfiltered off
  10. customdried
  11. custom2.8 g (100%) of 3-{3-[(5,5,8,8- tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbonyl) amino]phenyl}acrylic acid, with a melting point of 215-6° C., are collected

Sources & evidence

ORD record
ord-846b04efd2d64a61abc023c895c2db4e
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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