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

HRID 502869Notes

Reaction equation

HRID 502869 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-63c774a22b98469684e7eac1742fb965
Source dataset
uspto-grants-2010_08
Patent number
US07776882B2

Reaction notes

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