Hydrochloric Acid → 2-formyl-1H-indole-3-carbonitrile

HRID 1362352ノート

反応式

HRID 1362352 の反応式
Cl.C(OC(OCC)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]#[N:16])=[C:7]1[CH:17]=[O:18])C.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH:17]([C:7]1[NH:6][C:14]2[C:9]([C:8]=1[C:15]#[N:16])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:18]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 592776141-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile

生成物 1

HCID 592775632-formyl-1H-indole-3-carbonitrile収率 84.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

Hydrochloric acid (4 mL, 20%) was added to a THF (100 mL) solution of 1-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile (5.33 g, 19.57 mmol) at 0° C. The mixture was stirred at 20° C. for 41 h then treated with 5% aqueous K2CO3 (25 mL). The reaction mixture was concentrated to 50 mL and treated with methylene chloride (200 mL). The organic layer was washed with water, dried and evaporated to afford the title compound (2.81 g, 84%). 1H NMR (300 MHz, DMSO-d6, δ): 13.20 (s, br, 1H), 10.02 (s, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.63 (d, J=7.7 Hz, 1H), 7.51 (t, J=7.1 Hz, 1H), 7.37 (t, J=7.5 Hz, 1H).

後処理

  1. concentrationThe reaction mixture was concentrated to 50 mL
  2. additiontreated with methylene chloride (200 mL)
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated

出典と根拠

ORDレコード
ord-b29bf17a928a48a9aecf8c4eae6494d8
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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