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

HRID 45791ノート

反応式

HRID 45791 の反応式
[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

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67975686HCID 67975686、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-69672cf869ec4487bcf55f83dd5f4f2b
出典データセット
uspto-grants-2013_09
特許番号
US08541576B2

反応ノート

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