HCID 4442037, compound → HCID 10980947, compound

HRID 1602302Notes

Reaction equation

HRID 1602302 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([C:9]1([OH:32])[C:29]2[CH:28]=[C:27]3[N:15]([CH2:16][C:17]4[C:18]3=[N:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[CH:26]=4)[C:14](=[O:30])[C:13]=2[CH2:12][O:11][CH:10]1[OH:31])[CH3:8]>O.C(O)(=O)C>[CH:10]([O:11][CH2:12][C:13]1[C:14](=[O:30])[N:15]2[C:27](=[CH:28][C:29]=1[C:9](=[O:32])[CH2:7][CH3:8])[C:18]1=[N:19][C:20]3[C:25]([CH:26]=[C:17]1[CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:31]

Participants

5

Reactant 2

HCID 4442037HCID 4442037, compoundHCID 23667635Sodium periodate

Product 1

HCID 10980947HCID 10980947, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium Metaperiodate (14 g, 65 mmol) in water (140 ml) is added drop-wise to a suspension of 4-ethyl-3,4-dihydroxy-1H-pyrano [3',4': 6,7] indolizino [1,2-b] quinoline-14(4H,12H)-one (13.4 g, 38 mmol) in glacial acetic acid (720 ml) and the resulting solution is agitated for one hour at ambient temperature. The reaction mixture is then poured into a mixture of ice/water (650 ml) and the resulting suspension is agitated for one half-hour then filtered and washed successively with water, isopropyl alcohol, and etherdiethyl alcohol, which, after drying under reduced pressure, the sought compound (11.5 g) in the form of a pale yellow solid, m.p. >200° C. (d).

Workup

  1. stirringthe resulting suspension is agitated for one half-hour
  2. filtrationthen filtered
  3. washwashed successively with water, isopropyl alcohol, and etherdiethyl alcohol, which
  4. customafter drying under reduced pressure

Sources & evidence

ORD record
ord-191e1b8a58e14f12b130af0823d70202
Source dataset
uspto-grants-1999_11
Patent number
US05981542

Reaction notes

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