Diethyl Ether → CP-376395

HRID 1637688ノート

反応式

HRID 1637688 の反応式
CO[C:3](=O)[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26].[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>C1COCC1>[CH3:3][C:4]1[C:5]([O:17][C:18]2[C:19]([CH3:26])=[CH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[N:6][C:7]([CH3:16])=[CH:8][C:9]=1[NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 232165764-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

生成物 1

HCID 9862166CP-376395収率 102.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (prepared as described in Preparation F, 29 mg, 0.078 mmol) and AlCl3 (10 mg,0.078 mmol) in dry THF was added 1 M LiAlH4 in diethyl ether (0.31 ml, 0.31 mmol) at room temperature. After stirring for 10 min, the mixture was heated under reflux for 2 hr. The mixture was quenched with 0.2 ml of water, 0.2 ml of 1N NaOH and 0.4 ml of water and 10 ml of dry THF and stirred for 15 min. The mixture was filtered through Celite® and washed with chloroform. The filtrate was dried over dry sodium sulfate, filtered and concentrated to dryness to give 26 mg (93%) of white solid. 1H NMR (CDC13) δ 6.85(s,2H), 6.08(s,1H), 3.72(d,NH, 1H), 3.35(m,1H), 2.30(s,3H), 2.16(s,3H), 2.13 (s,3H), 2.05(s, 6H), 1.45-1.75(m,4H), 0.98(t,6H) ppm. The corresponding HCl salt was prepared and triturated with diethyl ether to give white solid, mp.212-215° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customThe mixture was quenched with 0.2 ml of water, 0.2 ml of 1N NaOH and 0.4 ml of water and 10 ml of dry THF
  4. stirringstirred for 15 min
  5. filtrationThe mixture was filtered through Celite®
  6. washwashed with chloroform
  7. dry with materialThe filtrate was dried over dry sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-06e495955b5f4452b9a7c5b75bcf091c
出典データセット
uspto-grants-2000_03
特許番号
US06043260

反応ノート

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