Water → HCID 22593236, compound

HRID 1760897Notes

Reaction equation

HRID 1760897 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:8]([O:25][CH3:26])[CH:7]=1)([O-])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:1][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:8]([O:25][CH3:26])[CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 69532064HCID 69532064, compound

Product 1

HCID 22593236HCID 22593236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Nitro-2-(4-dodecyloxy-3-methoxyphenyl)ethene (5.7 g; 16 mmol) is suspended in THF ((100 ml) under a protective gas atmosphere. LAH solution (1M in THF; 56 ml, 56 mmol) is then slowly added dropwise. When the addition is complete, heating at reflux is carried out for 2 hours and stirring is then carried out for a further 16 hours at 25° C. Excess LAH is then decomposed with water (8 ml), 15% sodium hydroxide solution (8 ml) and again with water (24 ml). The suspension is stirred for a further 30 minutes at 25° C. and then filtration is carried out. The filtrate is concentrated to dryness by evaporation, and the brown residue is taken up in 10% aqueous hydrochloric acid (12 ml) and washed with tert-butyl methyl ether (3×10 ml). The aqueous phase is rendered alkaline with 15% sodium hydroxide solution (6 ml) and extracted with tert-butyl methyl ether (3×10 ml). The organic extracts are combined, washed with water and saturated sodium chloride solution, and dried over K2CO3. Filtration is followed by concentration to dryness by evaporation, and freeze-drying is carried out from tert-butyl alcohol/water (4:1) with the addition of hydrochloric acid.

Workup

  1. additionWhen the addition
  2. temperatureheating
  3. temperatureat reflux
  4. waitis then carried out for a further 16 hours at 25° C
  5. stirringThe suspension is stirred for a further 30 minutes at 25° C.
  6. filtrationfiltration
  7. concentrationThe filtrate is concentrated to dryness by evaporation
  8. washwashed with tert-butyl methyl ether (3×10 ml)
  9. extractionextracted with tert-butyl methyl ether (3×10 ml)
  10. washwashed with water and saturated sodium chloride solution
  11. dry with materialdried over K2CO3
  12. filtrationFiltration
  13. concentrationis followed by concentration to dryness by evaporation
  14. customfreeze-drying
  15. additionis carried out from tert-butyl alcohol/water (4:1) with the addition of hydrochloric acid

Sources & evidence

ORD record
ord-88940fd3ca414f5c99cd283205c92d20
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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