Hydrochloric Acid → Methyl [2-(aminomethyl)phenyl]acetate--hydrogen chloride (1/1)

HRID 1612399Notes

Reaction equation

HRID 1612399 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[N:12].[ClH:14].[H][H]>CO>[ClH:14].[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][NH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1512623Methyl(2-cyanophenyl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 21185367Methyl [2-(aminomethyl)phenyl]acetate--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3a in methanol (0.2 M) was added palladium, 10 weight % (dry basis) on activated carbon, wet, (0.1 eq) and concentrated hydrochloric acid (3.5 eq). The reaction mixture was shaken overnight on a Parr reactor, with hydrogen pressure equal to 70 psi. The reaction mixture was filtered through celite, concentrated in vacuo then triturated with ether. The product was obtained as a white solid. (85%) 1H NMR (300 MHz, DMSO-d6) δ 8.66 (br s, 2H), 7.55 (m, 1H), 7.32 (m, 3H), 4.01 (m, 2H), 3.89 (s, 2H), 3.61 (s, 3H).

Workup

  1. dry with materialpalladium, 10 weight % (dry basis) on activated carbon
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customthen triturated with ether
  5. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-e347ec0b60d144beb2bbe78e3b45da33
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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