2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → ethyl 1-(2-hydroxyethyl)-8-methoxy-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 45791Notes

Reaction equation

HRID 45791 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([O:17][CH3:18])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:5]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([O:17][CH3:18])[N:12]=[CH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:5]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67975686HCID 67975686, compound

Product 1

HCID 67975382ethyl 1-(2-hydroxyethyl)-8-methoxy-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of ethyl 1-(2-hydroxyethyl)-8-methoxy-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate 1.2 g (3.76 mmol) in toluene (20 ml), 500 mg (2.2 mmol) 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile were added. The mixture was submitted to microwave irradiation at 100° for 3 hours in a sealed vial. The volatiles were evaporated, the crude was dissolved with ethyl acetate and portioned with sat. NaHCO3, the organic layer concentrated to dryness. The residue was purified by chromatography (ethyl acetate/hexane 7/3) to afford the desired compound 520 mg (46%). HRMS (ESI) calcd for C15H16N4O4 [M+H]+ 317.3119 found 317.3126.

Workup

  1. additionwere added
  2. customirradiation at 100° for 3 hours in a sealed vial
  3. customThe volatiles were evaporated
  4. dissolutionthe crude was dissolved with ethyl acetate
  5. concentrationthe organic layer concentrated to dryness
  6. customThe residue was purified by chromatography (ethyl acetate/hexane 7/3)

Sources & evidence

ORD record
ord-69672cf869ec4487bcf55f83dd5f4f2b
Source dataset
uspto-grants-2013_09
Patent number
US08541576B2

Reaction notes

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