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Ammonium Chloride → 6-Phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-ylamine

HRID 252446
ノート
印刷プレビュー

反応式

HRID 252446 の反応式
C(OP([CH:9]([C:21]#[N:22])[CH:10]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH2:11][CH2:12][CH:13]=[CH2:14])(=O)OCC)C.[N+:23]([C:26]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:30][C:27]=1[CH:28]=O)([O-])=O.[Cl-].[NH4+]>C1COCC1>[O:34]([C:31]1[CH:30]=[C:27]2[C:26](=[CH:33][CH:32]=1)[N:23]=[C:21]([NH2:22])[C:9]([CH:10]([CH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[CH2:11][CH2:12][CH:13]=[CH2:14])=[CH:28]2)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 442030822-Nitro-5-phenoxybenzaldehydeHCID 59428163[1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

生成物 1

HCID 672683566-Phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-ylamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the oil isolated in Step B (23.28 g, 70.7 mmol) in THF (100 mL) at −78° C., LHDMS (1.0 M, 84.8 mL, 84.8 mmol) was added slowly. The reaction mixture was then stirred at room temperature for 1 hour. A solution of 2-nitro-5-phenoxybenzaldehyde (20.63 g, 75.5 mmol) in THF (100 mL) was added. The reaction mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride (200 mL) was added. The reaction mixture was extracted with ethyl acetate three times. The combined organic extracts were washed with brine and dried over magnesium sulfate. The reaction mixture was filtered and concentrated to yield a colorless oil which was a mixture of cis-[2-(2-nitro-5-phenoxy-benzylidene)-3-(tetrahydro-pyran-4-yl)-hept-6-enenitrile] and trans-[2-(2-nitro-5-phenoxy-benzylidene)-3-(tetrahydro-pyran-4-yl)-hept-6-enenitrile].

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionThe reaction mixture was extracted with ethyl acetate three times
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated
  7. customto yield a colorless oil which

出典と根拠

ORDレコード
ord-e76e464e68ef47c9b8630530c1b51755
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07868022B2

反応ノート

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