Ammonium Chloride → HCID 58531369, compound

HRID 1889709Notes

Reaction equation

HRID 1889709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](OC)=[O:15])[C:9]=2[O:18][CH3:19])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[C:9]=2[O:18][CH3:19])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 58531509HCID 58531509, compound

Product 1

HCID 58531369HCID 58531369, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4′-chloro-2-methoxybiphenyl-3-carboxylate (1.7 g, 6.14 mmol, 1.0 eq) was dissolved in dry THF under nitrogen and cooled to 0° C. Then 1M LAH solution (0.349 g, 9.22 mmol, 1.5 eq) was slowly added. The reaction mixture was stirred for 1 h at 0° C. Saturated aqueous NH4Cl solution was added dropwise at 0° C. and the resulting mixture was stirred for 30 minutes. The mixture was further diluted with water and extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum to give the desired product (1.4 g, 92%). 1H NMR (400 MHz, CD3OD) δ 3.42 (s, 3H), 3.88-3.90 (d, 1H), 4.77-4.78 (m, 2H), 7.18-7.21 (t, 1H), 7.26-7.29 (t, 1H), 7.34-7.43 (m, 3H), 7.51-7.54 (t, 2H). MS (ESI): 248.2 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-da3a9f0ff3504524ad2c62f33b9b75ce
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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