Hydrochloric Acid → 1-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

HRID 1410799ノート

反応式

HRID 1410799 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7](I)[N:6]=1)=[O:4].[C:25]([Cu])#[N:26].C(Cl)Cl.Cl>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7]([C:25]#[N:26])[N:6]=1)=[O:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 867141181-Benzyl-8-hydroxy-5-iodo-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl esterHCID 178418546HCID 178418546、化合物

生成物 1

HCID 682972101-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester収率 61.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1-benzyl-8-hydroxy-5-iodo-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester (113 mg, 0.26 mmol) and CuCN (46 mg, 0.52 mmol) in DMF (3 mL) was heated at 120° C. for 8 min. After cooling to r.t., CH2Cl2 (50 mL) and 4 M HCl (50 mL) were added. The mixture was stirred vigorously until no more solid was present. The aqueous layer was extracted with additional CH2Cl2, and organic layers were combined, washed with water, and dried over MgSO4. After evaporating the solvent, the crude product was purified by silica gel chromatography (100% CH2Cl2) to give 54 mg of the title compound. MS: (−) m/z 334.30 (M−1).

後処理

  1. temperatureAfter cooling to r.t.
  2. extractionThe aqueous layer was extracted with additional CH2Cl2, and organic layers
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe crude product was purified by silica gel chromatography (100% CH2Cl2)

出典と根拠

ORDレコード
ord-61d58bdd38c34eab9a2bf48087dff461
出典データセット
uspto-grants-2014_12
特許番号
US08921389B2

反応ノート

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