Formamidine → HCID 178487763, compound

HRID 1852283Notes

Reaction equation

HRID 1852283 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:13](N)=[NH:14]>O>[CH3:12][O:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4]([OH:5])=[N:14][CH:13]=[N:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 68047FormamidineHCID 3510102-Amino-4-methoxybenzoic acid

Product 1

HCID 178487763HCID 178487763, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 2-amino-4-methoxy benzoic acid (8.6 g, 51.4 mmol) in 2-dimethoxy ethane (100 ml) was added formamidine (10.71 g, 103 mmol). The reaction mass was heated to 125° C. 18 h. The reaction mass was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (6.92 g, 74.8%) as pale yellow solid. 1H NMR (400 MHz, DMSO): δ ppm 12.10 (br, s, 1H), 8.06 (s, 1H), 8.03-8.01 (d, J=8 Hz, 1H), 7.11-7.09 (m, 2H), 3.89 (s, 3H);

Workup

  1. custom18 h
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-e60692753d6c4e2fb25f772f16ce0df7
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…