Acetic Acid → HCID 13520146, compound

HRID 484804Notes

Reaction equation

HRID 484804 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])[NH2:6].C=O.[C:23]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[CH3:23][NH:6][C:5]1[CH:7]=[CH:8][C:9]([N:10]2[C:11](=[O:20])[C:12]3=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]3[C:14]2=[O:15])=[C:3]([CH3:2])[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 131714297HCID 131714297, compound

Product 1

HCID 13520146HCID 13520146, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1.4 g of the product aniline of Example 31 and 2.5 ml of 37% aqueous formaldehyde in 19 ml of acetonitrile was added in portions 0.62 g of sodium cyanoborohydride. After twenty minutes the solution was adjusted to pH 7 with glacial acetic acid and stirred for another hour. Ice was added, acetonitrile was removed in vacuo, and the mixture was partitioned between water and dichloromethane. The organic layer was dried over potassium carbonate, filtered, and concentrated to an oil which was chromatographed on a silica gel column using dichloromethane as eluent. Fractions containing the title compound were concentrated to give a solid, m.p. 159°-161°. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. additionIce was added
  2. customacetonitrile was removed in vacuo
  3. customthe mixture was partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil which
  7. customwas chromatographed on a silica gel column
  8. additionFractions containing the title compound
  9. concentrationwere concentrated
  10. customto give a solid, m.p. 159°-161°

Sources & evidence

ORD record
ord-b9d5d3c6d2914224b5dfbf3f272f585f
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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