2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Dimethyl 4-ethyl-6-methoxy-3-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate

HRID 1421263Notes

Reaction equation

HRID 1421263 reaction equation
[CH2:1]([C:3]1[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][N:6]2[C:11]=1[CH:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2)[CH3:2].[C:22]([C:28]([O:30][CH3:31])=[O:29])#[C:23][C:24]([O:26][CH3:27])=[O:25].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7]([CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:22]([C:28]([O:30][CH3:31])=[O:29])=[C:5]3[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12980Dimethyl acetylenedicarboxylateHCID 11108777HCID 11108777, compound

Product 1

HCID 11825967Dimethyl 4-ethyl-6-methoxy-3-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-ethyl-7-methoxy-2-(4-methoxyphenyl)indolizine (25.0 g, 0.089 mol) in 800 ml of toluene was stirred in an ice bath, while dimethyl acetylenedicarboxylate (12.6 ml, 0.103 mol) was added dropwise. When the starting material had been consumed according to TLC, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (21.18 g, 0.093 mol) was added in portions. When the addition was complete, the mixture was refluxed for one hour. The resulting hydroquinone was filtered off, and the filtrate was concentrated to dryness. The residue was triturated with petroleum ether (40-60) and isolated to afford 33.8 g (92%) of the title compound. M.p. 153-5° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.36 (t, 3H), 3.07 (q, 2H), 3.76 (s, 3H), 3.86 (s, 3H), 3.89 (s, 3H), 4.10 (s, 3H), 7.15 (d, 2H), 7.53 (d, 2H), 7.84 (d, 1H), 8.00 (d, 1H). (Compound 1).

Workup

  1. additionwas added dropwise
  2. customWhen the starting material had been consumed
  3. additionwas added in portions
  4. additionWhen the addition
  5. temperaturethe mixture was refluxed for one hour
  6. filtrationThe resulting hydroquinone was filtered off
  7. concentrationthe filtrate was concentrated to dryness
  8. customThe residue was triturated with petroleum ether (40-60)
  9. customisolated

Sources & evidence

ORD record
ord-090fe8e5960b4846bf0b59ae15177ac6
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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