Ammonium Chloride → HCID 23130711, compound

HRID 2080259Notes

Reaction equation

HRID 2080259 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[CH:27]3)=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O(C1SC(CNC(C2C=C3CCNC3=NC=2)=O)=CC=1)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][CH2:22][C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[CH:27]3)=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 58387908HCID 58387908, compoundHCID 58875323HCID 58875323, compound

Product 1

HCID 23130711HCID 23130711, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (52 mg, 1.37 mmol) in tetrahydrofuran (10 mL) was added a solution of quinoline-6-carboxylic acid (4-benzyloxyphenyl)-amide described in Preparation Example Z+-2 (194 mg, 19%) in tetrahydrofuran, and the solution was stirred under reflux for 3 hours. The reaction solution was allowed to room temperature, an aqueous solution of saturated ammonium chloride was added thereto, the solution was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate), and the title compound (62 mg, 33%) was obtained as a pale yellow solid.

Workup

  1. temperatureunder reflux for 3 hours
  2. customwas allowed to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ba473af80bcd44309e41782504037ae3
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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