Acetic Acid → HCID 14677300, compound

HRID 1165800Notes

Reaction equation

HRID 1165800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:26][CH3:27])[C:10]=2[CH:9]=1.[BH4-].[Na+].C(O)(=O)C.C1(C)C=CC=CC=1.C(OC(C)C)(C)C>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][CH:23]([OH:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:26][CH3:27])[C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 14677289HCID 14677289, compoundHCID 22228022HCID 22228022, compound

Product 1

HCID 14677300HCID 14677300, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.3 g (2.13 mmole) 4-(2-chlorophenyl)-6-ethyl-1,2,3,6-tetrahydro-1,3-dioxopyrrolo[3,4-c]carbazole (Example 2a) are suspended in 20 ml 90% methanol, a solution of 0.16 g (4.23 mmole) sodium borohydride in 5 ml methanol added dropwise thereto with vigorous stirring and stirred for 5 days at room temperature. The excess sodium borohydride is decomposed with acetic acid, the solvent is distilled off, and the crystalline residue is chromatographed on silica gel with toluene/ethyl acetate 1:1. The fraction with the Rf of 0.3 is isolated, stirred up with toluene/diisopropyl ether, and the crystals formed are filtered off. One obtains 4-(2-chlorophenyl)-6-ethyl-1,2,3,6-tetrahydro-1-hydroxy-3-oxopyrrolo[3,4-c]carbazole (Example 4a) in the form of pale beige crystals of the mp 225°-228° C.

Workup

  1. stirringstirred for 5 days at room temperature
  2. distillationthe solvent is distilled off
  3. customthe crystalline residue is chromatographed on silica gel with toluene/ethyl acetate 1:1
  4. customThe fraction with the Rf of 0.3 is isolated
  5. customthe crystals formed
  6. filtrationare filtered off

Sources & evidence

ORD record
ord-b4ccba509204440396972398b3e8eab2
Source dataset
uspto-grants-1990_03
Patent number
US04912107

Reaction notes

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