Hydrochloric Acid → N-(4-methoxyphenyl)Glycine

HRID 394781Notes

Reaction equation

HRID 394781 reaction equation
C([N:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH2:4][C:5]([OH:7])=[O:6])C.O.[OH-].[Li+].Cl>C1COCC1.O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([NH:3][CH2:4][C:5]([OH:7])=[O:6])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69691057HCID 69691057, compound

Product 1

HCID 4106784N-(4-methoxyphenyl)GlycineYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 19.59 g (108 mmol) of ethyl N-(4-methoxyphenyl)glycine in 100 mL of THF under N2 was added 5.44 g (130 mmol) of lithium hydroxide monohydrate in 25 mL water. After 15 hours, the mixture was reduced to ½ the original volume in vacuo and then acidified with concentrated hydrochloric acid to ph 3 and a precipitate formed. The solid was collected and washed with 100 mL water, then dried in vacuo to give 9.92 g (51%) of the desired compound as a off-white solid. 1H NMR (CDCl3): δ 6.68 (d, J=8.8, 2H); 6.49 (d, J=8.8, 2H); 3.73 (s, 2H); 3.64 (s, 3H); 2.49 (br s, 2H).

Workup

  1. customa precipitate formed
  2. customThe solid was collected
  3. washwashed with 100 mL water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-07f0ba39ecd74b3db36390a62e6d24bc
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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