Hydrochloric Acid → 1-(3-Hydroxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

HRID 1672504Notes

Reaction equation

HRID 1672504 reaction equation
COC[O:4][CH:5]([CH3:29])[C:6](=[O:28])[CH2:7][N:8]1[C:13]([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]([C:21]([F:24])([F:23])[F:22])=[C:10]([C:25]#[N:26])[C:9]1=[O:27].Cl>CO>[OH:4][CH:5]([CH3:29])[C:6](=[O:28])[CH2:7][N:8]1[C:13]([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]([C:21]([F:24])([F:22])[F:23])=[C:10]([C:25]#[N:26])[C:9]1=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 673402801-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

Product 1

HCID 673403991-(3-Hydroxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrileYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile (0.191 g, 0.47 mmoles) was dissolved into 25 mL of anhydrous MeOH and to this solution was added HCl (2.0 M solution in diethyl ether, 5.0 mL). The mixture was then stirred at room temperature for 2 hours. After this period the reaction mixture was evaporated in vacuo and was purified using flash silica chromatography (0-60% EtOAc/Hexane) to yield 0.16 g (93% yield) of 1-(3-Hydroxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile as a yellow residue. 1H-NMR (CDCl3): δ7.42-7.35 (m, 2H), 7.14-7.08 (m, 2H), 6.50 (m, 1H), 5.06 (d, J=17.2 Hz, 1H), 4.92 (d, J=17.2 Hz, 1H), 4.39-4.31 (m, 1H), 3.48 (bs, 1H), 2.40 (s, 3H), 1.28 (d, J=6.8 Hz, 3H).

Workup

  1. customAfter this period the reaction mixture was evaporated in vacuo
  2. customwas purified

Sources & evidence

ORD record
ord-00f557fee47b4c98affc3cde901bb8f2
Source dataset
uspto-grants-2011_08
Patent number
US07998986B2

Reaction notes

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