Water → HCID 178520005, compound

HRID 1733222Notes

Reaction equation

HRID 1733222 reaction equation
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[C:7]([O:18]C(=O)C)[N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.C(=O)=O.CC(C)=O.O>O1CCCC1>[CH:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[C:7]([OH:18])[N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 15573075HCID 15573075, compoundHCID 18522661Acetone cardiceHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178520005HCID 178520005, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of dry tetrahydrofuran were dissolved 135 mg of the product of Example 6, followed by addition of 2 ml of di-isobutyl-aluminum hydride. The reaction mixture was allowed to stand with dry ice-acetone cooling for 2 hours and then poured into water. The precipitated reagent was removed, the solvent removed by distillation and the residue recrystallized from water-methanol to yield 10 mg of the title compound melting at 290°-295° C. (decomp.). Mol. wt. (based on mass spectrum) 212. IR absorption spectrum: 3300, 1640, 1620, 1600 cm-1. UV absorption spectrum (MeOH): 420, 292, 282, 262 mμ. NMR spectrum (DMSO-d6): 10.1 ppm, 1H (CHO), 7.7 ppm, 1H (4-H), 8.2 ppm, 1H, 7.2-7.6 ppm, 3H.

Workup

  1. customThe precipitated reagent was removed
  2. customthe solvent removed by distillation
  3. customthe residue recrystallized from water-methanol

Sources & evidence

ORD record
ord-28f826b1c372404999709e758d264568
Source dataset
uspto-grants-1980_12
Patent number
US04241064

Reaction notes

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