Water → HCID 59165959, compound

HRID 2420886Notes

Reaction equation

HRID 2420886 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[N:6][CH:5]=1.[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]3[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:17])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 737487Methyl 6-aminonicotinate

Product 1

HCID 59165959HCID 59165959, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-aminonicotinic acid methyl ester (1.1 g, 7.2 mmol) and phthalic anhydride (1.2 g, 7.9 mmol) in anhydrous toluene was heated at reflux overnight in a Dean-Stark apparatus until no more water was collected. The reaction mixture was concentrated under vacuum. The residue was dissolved in ethyl acetate (50 mL) and was washed with brine and water. The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to give 6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-nicotinic acid methyl ester (1.2 g, 60%), which was directly used in the next step without further purification. 1H NMR (300 MHz, d-DMSO) δ 9.12 (d, J=1.5 Hz, 1H), 8.52 (dd, J=2.1, 8.4 Hz, 1H), 8.03-7.92 (m, 4H), 7.72 (d, J=7.8 Hz, 1H), 3.91 (s, 3H).

Workup

  1. customwas collected
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  4. washwas washed with brine and water
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2f0869135377432e938d109413baed0e
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

Loading…