Sodium Bicarbonate → 8-Hydroxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

HRID 61904ノート

反応式

HRID 61904 の反応式
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:21])([CH3:20])[C:7]=2[CH:22]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:20])([CH3:21])[C:7]=2[CH:22]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 668342278-Methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

生成物 1

HCID 668350828-Hydroxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one収率 54.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
178 °C

実験手順

Mixture of 8-methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b] fluoren-5-one (Compound GT15-4, 25 mg) and pyridine hydrochloric acid salt (492 mg) was stirred and heated at 178° C. overnight. The reaction mixture was cooled, and added with water. The mixture was neutralized with saturated aqueous solution of sodium bicarbonate and extracted with DCM. The organic layer was washed with saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (DCM/MeOH) to obtain the title compound (13 mg, 54%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residues were purified by silica gel column (DCM/MeOH)

出典と根拠

ORDレコード
ord-de8fb03427b34e699e0b38819f1f8c41
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

反応ノート

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