Methylamine → HCID 59300078, compound

HRID 2236418Notes

Reaction equation

HRID 2236418 reaction equation
[CH3:1][NH2:2].[C:3]1(=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5](=[O:13])[O:4]1>C1COCC1>[CH3:1][NH:2][C:5](=[O:13])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[C:3]([OH:4])=[O:14]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 12801Homophthalic anhydride

Product 1

HCID 59300078HCID 59300078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To 20 ml of 2.0 M methylamine in THF is added 1.62 g (10 mmol) of isochroman-1,3-dione at 0° C. The mixture is stirred at 25° C. for 45 m and concentrated to dryness. The residue is stirred in 40 ml of 0.3 N HCl. The white solid is filtered off, washed with water, and dried to give 1.74 g (90%); 1H NMR (DMSO-d6) δ 7.80 (s, 1H), 7.81 (s, 1H), 7.40 (m, 3H), 3.83 (s, 2H), 2.57 (s, 3H); MS (ES−) m/z 192.1 (M−H)−1: Analysis for C10H11NO3: Calcd: C, 62.17; H, 5.74; N, 7.25. Found: C, 62.16; H, 5.81; N, 7.24

Workup

  1. concentrationconcentrated to dryness
  2. stirringThe residue is stirred in 40 ml of 0.3 N HCl
  3. filtrationThe white solid is filtered off
  4. washwashed with water
  5. customdried
  6. customto give 1.74 g (90%)

Sources & evidence

ORD record
ord-1de338c3d72d4344bcbf3c35e1c0b7c9
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…