4-Aminobenzoic Acid → 4-[(N,N-dimethylglycyl)amino]benzoic acid

HRID 252829Notes

Reaction equation

HRID 252829 reaction equation
Cl.[CH3:2][N:3]([CH2:5][C:6](Cl)=[O:7])[CH3:4].C(=O)(O)[O-].[Na+].[NH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1>C(#N)C>[CH3:2][N:3]([CH2:5][C:6]([NH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 516892Sodium BicarbonateHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 195774524-[(N,N-dimethylglycyl)amino]benzoic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N,N-dimethylaminoacetyl chloride hydrochloride (137, 10.1 g, 64.2 mmol) in acetonitrile (300 ml.) was added powdered sodium bicarbonate (11.9 g, 141 mmol) followed by 4-aminobenzoic acid (138, 9.68 g, 70.6 mmol). The mixture was vigorously stirred over 16 h at r.t. and acetonitrile was decanted. The remaining gum was triturated with methanol and filtration afforded the title compound 139 (10.9 g, 76% yield). 1H NMR: (400 MHz, DMSO-d6) δ(ppm): 10.21 (s, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.6 Hz, 2H), 4.17 (bs, 2H), 2.27 (s, 6H). LRMS: (m/z): 223.3 (MH+).

Workup

  1. customacetonitrile was decanted
  2. filtrationThe remaining gum was triturated with methanol and filtration

Sources & evidence

ORD record
ord-c72a09c1b6824b8498fbb3522b447b16
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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