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Ethyl bromoacetate → HCID 21892018, compound

HRID 1884063
Notes
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Reaction equation

HRID 1884063 reaction equation
[CH3:1][C:2]1[C:3](=[O:23])[N:4]2[C:16](=[CH:17][C:18]=1[C:19](=[O:22])[CH2:20][CH3:21])[C:7]1=[N:8][C:9]3[C:14]([CH:15]=[C:6]1[CH2:5]2)=[CH:13][CH:12]=[CH:11][CH:10]=3.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>O1CCCC1.[Zn].C([O-])(=O)C.[Ag+].C(O)C>[OH:22][C:19]([C:18]1[CH:17]=[C:16]2[N:4]([CH2:5][C:6]3[C:7]2=[N:8][C:9]2[C:14]([CH:15]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3](=[O:23])[C:2]=1[CH3:1])([CH2:20][CH3:21])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7748Ethyl bromoacetateHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 1940068-Methyl-7-propanoylindolizino[1,2-b]quinolin-9(11H)-oneHCID 5462222Potassium

Product 1

HCID 21892018HCID 21892018, compoundYield 16.6%

Reagents, catalysts & solvents 4

HCID 11246
Silver acetate
Catalyst
HCID 23994ZincCatalyst
HCID 702EthanolSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of zinc (1.25 g, 19.1 mmol), 8-methyl-7-propionylindolizino[1,2-b]quinoline-9-(11H)-one (500 mg, 1.43 mmol, as obtained by Kingsburry, W. D., Tetrahedron Lett. 29:6847 (1988)) and silver acetate (250 mg, 1.50 mmol) in anhydrous tetrahydrofuran (10 ml) is agitated at ambient temperature under an argon atmosphere. After 10 minutes, the reaction mixture is activated by the dropwise addition of a molar solution of chlorodiethylalumninium (10 ml, 10 mmol), then ethyl bromoacetate (1.25 ml, 11.3 mmol) is added dropwise and the resultant mixture is left to react for another 5 hours. The reaction is stopped by the successive addition of ethyl alcohol (10 ml) and a saturated solution of potassium and sodium tartrate (10 ml). The resultant mixture is agitated for another hour, filtered and concentrated under reduced pressure. The residue is taken up in dichloromethane (30 ml), washed with water, dried, concentrated and purified by column chromatography (SiO2, CH2Cl2/MeOH:98/2), which produces 93 mg (15%) of desired product in the form of a pale yellow solid, m.p. 185-188° C.

Workup

  1. additionthe reaction mixture is activated by the dropwise addition of a molar solution of chlorodiethylalumninium (10 ml, 10 mmol)
  2. customto react for another 5 hours
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. custompurified by column chromatography (SiO2, CH2Cl2/MeOH:98/2), which

Sources & evidence

ORD record
ord-baad2c3975bf4b60a7eb2f421136156e
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06762301B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes