Methylamine → HCID 11783147, compound

HRID 1698856Notes

Reaction equation

HRID 1698856 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:34])[CH:20]=[C:21]([C:23]([N:25]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:26][CH:27]=[CH2:28])=[O:24])[CH:22]=1.CN>C(O)C>[NH2:3][O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:34])[CH:20]=[C:21]([C:23]([N:25]([CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:26][CH:27]=[CH2:28])=[O:24])[CH:22]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22946318HCID 22946318, compound

Product 1

HCID 11783147HCID 11783147, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethanol (50 mL) and phthalimide 18 (1.8 g, 3.7 mmol) was added 40% aqueous methylamine (25 mL). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated in vaczio and then chromatographed on silica gel to provide hydroxylamine 19 (0.5 g; 15% from 16). 1H NMR (300 MHz, CDCl3) δ 6.92 (s, 2H), 6.79 (s, 1H), 5.92 (bs, 1H), 5.40 (s, 2H), 5.17 (m, 2H), 4.04 (t, 2H), 3.88-4.03 (m, 3H), 3.82 (t, 2H), 3.88-4.03 (m, 3H), 3.82 (t, 2H), 2.01-2.12 (m, 2H), 1.4-1.9 (m, 8H).

Workup

  1. concentrationThe reaction mixture was concentrated in vaczio
  2. customchromatographed on silica gel

Sources & evidence

ORD record
ord-926d851697944a8998c68c126e817609
Source dataset
uspto-grants-2002_02
Patent number
US06344466B2

Reaction notes

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