Hydrochloric Acid → HCID 58551617, compound

HRID 2204160Notes

Reaction equation

HRID 2204160 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1F)[C:6]([OH:8])=[O:7])#[N:2].[CH3:13][O:14][CH2:15][CH2:16][OH:17].[H-].[Na+].Cl>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:17][CH2:16][CH2:15][O:14][CH3:13])[C:6]([OH:8])=[O:7])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 27739323-Cyano-4-fluorobenzoic acid

Product 1

HCID 58551617HCID 58551617, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

3-Cyano-4-fluorobenzoic acid (500 mg, 3.03 mmol), 2-methoxyethanol (461 mg, 6.06 mmol), and 60% w/w NaH (363 mg, 9.08 mmol) were combined in acetonitrile (15 mL) and the reaction mixture was heated at 70° C. overnight. The reaction mixture was made acidic by the addition of 1N HCl and was extracted with ethyl acetate. The organics were dried over sodium sulfate, evaporated and purified by column chromatography (0-10% methanol in dichloromethane) to yield 3-cyano-4-(2-methoxyethoxy)benzoic acid (625 mg, 93%). 1H NMR (400 MHz, CD3CN) δ 9.60 (s, 1H), 8.26 (d, J=1.9 Hz, 1H), 8.22 (dd, J=8.9, 2.2 Hz, 1H), 7.22 (d, J=8.9 Hz, 1H), 4.34 (dd, J=5.2, 3.7 Hz, 2H), 3.79 (dd, J=5.2, 3.6 Hz, 2H), 3.41 (s, 3H).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. customevaporated
  4. custompurified by column chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0a5b01a897294cb987ee6a247bd84dbe
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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