HCID 4442037, compound → HCID 10980947, compound

HRID 2414925Notes

Reaction equation

HRID 2414925 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-9719e0241ce340fb801234acd466f8d9
Source dataset
uspto-grants-2004_11
Patent number
US06815546B2

Reaction notes

Loading…