Hydrochloric Acid → HCID 24730102, compound

HRID 33537Notes

Reaction equation

HRID 33537 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[N:12]=1)=O.Cl>O1CCCC1.[Cl-].[Na+].O>[Cl:23][C:19]1[CH:18]=[C:17]([C:13]2[N:12]=[C:11]([CH2:9][OH:8])[CH:16]=[CH:15][CH:14]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 691068496-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 24730102HCID 24730102, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

399 mg (10.50 mmol) lithium aluminium hydride were given to 18 ml tetrahydrofuran (THF) and stirred at room temperature (r. t.) for 10 min. A solution of 1.30 g (5.25 mmol) 6-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester in 18 ml THF was added drop by drop at 0° C. within 15 min., and the mixture stirred for 2 h at 0° C. 32 ml brine were added slowly at 0° C. and stirred continued for 2 h. The mixture was adjusted to pH=5 by slowly addition of conc. HCl. A formed salt precipitate was isolated by filtration and washed with THF. The combined THF-solutions were evaporated, the residue extracted twice with ethyl acetate, the organic phase dried (sodium sulphate) and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:1) gave 0.45 g (35%) of [6-(3-Chloro-phenyl)-pyridin-2-yl]-methanol

Workup

  1. stirringthe mixture stirred for 2 h at 0° C
  2. stirringstirred
  3. waitcontinued for 2 h
  4. customA formed salt precipitate was isolated by filtration
  5. washwashed with THF
  6. customThe combined THF-solutions were evaporated
  7. extractionthe residue extracted twice with ethyl acetate
  8. dry with materialthe organic phase dried (sodium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-04e30e3269054c22a1d0241fd9ead72b
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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