Phosphoric Acid → N-(4-methoxyphenyl)Glycine

HRID 1507708Notes

Reaction equation

HRID 1507708 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:7][CH:6]=1.P(=O)(O)(O)O>CCO.C1COCC1.O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 6917278ethyl [(4-methoxyphenyl)amino]acetate

Product 1

HCID 4106784N-(4-methoxyphenyl)GlycineYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
40 °C

Procedure

2M NaOH (aq.) (149 mL, 0.30 mol) was added dropwise to a stirred solution of ethyl 2-((4-methoxyphenyl)amino)acetate (17) (59.2 g, 0.28 mol) in EtOH/THF (300 mL/80 mL). The reaction was stirred at 40° C. for 3 h. The mixture was diluted with water (100 mL) and phosphoric acid (85% wt in water) (35.9 g, 0.31 mol) was added to pH 3. The resulting brown precipitate was collected by filtration and washed with water (100 mL) and dried under vacuum to give 2-((4-methoxyphenyl)amino)acetic acid (18) (45.5 g, 84%) as a brown solid: m/z 182 (M+H)+ (ES+); 180 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 6.78-6.64 (m, 2H), 6.55-6.44 (m, 2H), 3.74 (s, 2H), 3.64 (s, 3H).

Workup

  1. additionwas added to pH 3
  2. filtrationThe resulting brown precipitate was collected by filtration
  3. washwashed with water (100 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-95860a4191104ad49e6cc7c6489abe9f
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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