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

HRID 502869
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반응식

HRID 502869 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-63c774a22b98469684e7eac1742fb965
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07776882B2

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