Methyl 4-aminobenzoate → HCID 14763211, compound

HRID 1271709Notes

Reaction equation

HRID 1271709 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[O:12]1[CH2:16][CH2:15][CH2:14][S:13]1(=[O:18])=[O:17]>>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:16][CH2:15][CH2:14][S:13]([OH:18])(=[O:17])=[O:12])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 14264Propane sultone

Product 1

HCID 14763211HCID 14763211, compoundYield 71%

Procedure

Methyl 4-aminobenzoate (1.34 g, 8.87 mmol) and [1,2]oxathiolane 2,2-dioxide (1.02 g, 8.36 mmol) were heated at 100–110° C for 1 h. The cooled residue was washed with 1N HCl and water and air-dried to give 4-(3-sulfo-propylamino)-benzoic acid methyl ester (1.62 g, yield: 71%). 1H NMR (DMSO-d6) δ 7.70 (d, J=8.7 Hz, 2H), 6.65 (d, J=8.7 Hz, 2H), 5.88 (br, s, NH+SO3H), 3.19 (t, J=7.0 Hz, 2H), 2.63 (t, J=7.3 Hz, 2H), 1.87 (quint, J=7.0 Hz, 2H). LC/MS (ESI) 256.22 (M+H)+, tR=2.21 min (10–90% MeOH in H2O with 10 mM NH4OAc in a 4-min run).

Workup

  1. washThe cooled residue was washed with 1N HCl and water
  2. customair-dried

Sources & evidence

ORD record
ord-16fb6aae2f2f471ca9dc4747d255860e
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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