Water → HCID 9954184, compound

HRID 2108049Notes

Reaction equation

HRID 2108049 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:12])[CH:10]=O)=[CH:4][C:3]=1[Cl:13].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29].O.CCCCCC>C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([CH:9]([CH2:10][NH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[OH:12])=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 13606650HCID 13606650, compoundHCID 15166946HCID 15166946, compound

Product 1

HCID 9954184HCID 9954184, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Amino-3,5-dichloro-α-oxobenzeneacetaldehyde (0.56 g) and 6-[2-(2-pyridinyl)ethoxy]hexanamine (0.40 g) were dissolved in benzene (10 ml) and heated under reflux for 1 h using a Dean-Stark water trap. The solution was cooled, evaporated in vacuo and the residue dissolved in methanol (10 ml). Sodium borohydride (0.38 g) was added portionwise at 0°-5° over 0.5 h with stirring. The solution was allowed to stand overnight then evaporated in vacuo. The residue was partitioned between water (50 ml) containing 2N sodium carbonate (4 ml) and ethyl acetate (60 ml). The organic phase was dried, evaporated in vacuo and the residue purified by FCC eluting with System C (90:10:1) to afford a gum. Trituration with hexane gave the title compound (85 mg) as a colourless powder m.p. 93°-96°, t.l.c. (System A 39:10:1) Rf 0.44.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureThe solution was cooled
  4. customevaporated in vacuo
  5. dissolutionthe residue dissolved in methanol (10 ml)
  6. additionSodium borohydride (0.38 g) was added portionwise at 0°-5° over 0.5 h
  7. customthen evaporated in vacuo
  8. customThe residue was partitioned between water (50 ml)
  9. additioncontaining 2N sodium carbonate (4 ml) and ethyl acetate (60 ml)
  10. customThe organic phase was dried
  11. customevaporated in vacuo
  12. customthe residue purified by FCC
  13. washeluting with System C (90:10:1)
  14. customto afford a gum

Sources & evidence

ORD record
ord-2d2c9424a02443468eda1960f9173d96
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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