HCID 4442037, compound → HCID 10980947, compound

HRID 1250712Notes

Reaction equation

HRID 1250712 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 dropwise to a suspension of 4-ethyl-3,4-dihydroxy-1,3,4,12-tetrahydro-14H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinolin-14-one (13.4 g, 38 mmol) in glacial acetic acid (720 ml) and the resultant solution is agitated for one hour at ambient temperature. The reaction mixture is then poured into an ice/water mixture (650 ml) and the resultant suspension is then agitated for half an hour then filtered and washed successively with water, isopropyl alcohol and diethyl ether, which allows the sought product (11.5 g) to be obtained, after drying under reduced pressure, in the form of a pale yellow solid m.p. >200° C. (d).

Workup

  1. filtrationthen filtered
  2. washwashed successively with water, isopropyl alcohol and diethyl ether, which
  3. customto be obtained
  4. dry with materialafter drying under reduced pressure, in the form of a pale yellow solid m.p. >200° C. (d)

Sources & evidence

ORD record
ord-c21bbba428b749198b46998b944dcf18
Source dataset
uspto-grants-2002_01
Patent number
US06339091B1

Reaction notes

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