Hydrochloric Acid → HCID 19863775, compound

HRID 1165062Notes

Reaction equation

HRID 1165062 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]([OH:21])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=2)[CH:7]=[CH:8][CH:9]=1)(O)=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[ClH:33]>C1COCC1.C(OCC)C.C(OCC)(=O)C>[ClH:33].[C:22]([C:13]1[CH:12]=[C:11]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:1][OH:2])[CH:5]=2)[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]=1[OH:21])([CH3:25])([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 601943-(3,5-DI-T-Butyl-4-hydroxyanilino)benzoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 19863775HCID 19863775, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.8 g quantity of the 4-(3-carboxyphenylamino)-2,6-di-tert-butylphenol prepared in Example 24 was dissolved in 30 ml of THF, and the solution was added dropwise at room temperature to a suspension of 1.7 g of LiAlH4 in 150 ml of ethyl ether with stirring. Then the resulting mixture was refluxed for 3.5 hours. After cooling, water-containing ethyl ether and then water were carefully added to the reaction mixture to decompose the excess LiAlH4. Subsequently the organic layer was separated, dried over MgSO4 and concentrated to give a crude product. The crude product was dissolved in 100 ml of ethyl ether, and 6 ml of 4N hydrogen chloride in ethyl acetate was added to the solution. The crystals thus precipitated were filtered, washed with ethyl ether and air-dried, giving 1.5 g of the title compound (Compound 31).

Workup

  1. temperatureThen the resulting mixture was refluxed for 3.5 hours
  2. temperatureAfter cooling
  3. customSubsequently the organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a crude product
  7. customThe crystals thus precipitated
  8. filtrationwere filtered
  9. washwashed with ethyl ether
  10. customair-dried

Sources & evidence

ORD record
ord-024605dfc77f44318faa6e83b9527a9a
Source dataset
uspto-grants-1990_03
Patent number
US04906662

Reaction notes

Loading…