Hydrochloric Acid → 6-Carbomethoxy-2'-nitro-flavanone

HRID 2083016

反応式

HRID 2083016 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[OH:15])[C:7]([O:9][CH2:10]C)=[O:8])(=[O:3])[CH3:2].[N+:16]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O)([O-:18])=[O:17].Cl>C(O)C.N1CCCCC1.O>[C:7]([C:6]1[CH:5]=[C:4]2[C:14](=[CH:13][CH:12]=1)[O:15][CH:21]([C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[N+:16]([O-:18])=[O:17])[CH2:2][C:1]2=[O:3])([O:9][CH3:10])=[O:8]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 12631990Ethyl 3-acetyl-4-hydroxybenzoate

生成物 1

HCID 213250586-Carbomethoxy-2'-nitro-flavanone

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8082Piperidine溶媒

実験手順

A mixture consisting of ethyl 3-acetyl-4-hydroxy-benzoate (6 g) and 2-nitro-benzaldehyde (5 g) dissolved in ethanol (100 ml and piperidine (100 ml) was kept at reflux temperature for 24 hours. The mixture was then cooled, diluted in water (800 ml), acidified with hydrochloric acid, extracted with ethylacetate, washed with water and evaporated to dryness to obtain as raw product, 6-carbomethoxy-2'-nitro-flavanone. This product (6.8 g) was dissolved in chloroform (40 ml) and treated with a solution of benzoyl peroxide (0.15 g) and N-bromosuccinimide (3.8 g) dissolved in chloroform (60 ml). The mixture was kept at reflux temperature for 4 hours, then evaporated to dryness under vacuum at low temperature; then the residue, dissolved in ethanol 95% (150 ml), was treated with sodium hydrate 4 N (25 ml) at room temperature for a night. After acidification with hydrochloric acid and filtration, 6-carboxy-2'-nitro-flavone (3.7 g) was obtained, which was subsequently treated with stannous chloride (20 g) in concentrated hydrochloric acid (15 ml) and glacial acetic acid (15 ml) at reflux temperature for 4 hours. After cooling, dilution with water, neutralisation with ammonium hydrate 28 Be, the precipitate was filtered to give, after crystallisation from dimethylformamide, 6-carboxy-2'-amino-flavone (1.8 g; m.p. > 300° C).

後処理

  1. temperatureat reflux temperature for 24 hours
  2. temperatureThe mixture was then cooled
  3. extractionextracted with ethylacetate
  4. washwashed with water
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-fc001214bac947099cc80eb868cb77cf
出典データセット
uspto-grants-1978_04
特許番号
US04083953

関連ノート

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