Methanol → HCID 59411458, compound

HRID 1624996Notes

Reaction equation

HRID 1624996 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[NH2:15][CH:16]([CH2:19][OH:20])[CH2:17][OH:18].C[OH:22].C(N([CH2:28][CH3:29])CC)C.C(Cl)Cl.[C:33](OC(=O)C)(=[O:35])[CH3:34]>CN(C)C1C=CN=CC=1>[C:33]([O:18][CH2:17][CH:16]([N:15]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[CH2:19][O:20][C:28](=[O:22])[CH3:29])(=[O:35])[CH3:34]

Participants

8

Reactant 6

HCID 887MethanolHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68294SerinolHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 59411458HCID 59411458, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

5-Nitro-isochromen-1-one (4.2 g, 0.022 mol) and serinol (2.0 g, 0.022 mol) were refluxed in methanol (40 mL, 1 mol) for 1 hour. TLC showed all the starting material consumed, triethylamine (20 mL, 0.1 mol) was added to the mixture and the reaction mixture was refluxed overnight. The volatiles were removed via rotovapor, and the residue was diluted with methylene chloride (100 mL, 2 mol). Acetic anhydride (9 g, 0.09 mol) and 4-dimethylaminopyridine (30 mg, 0.0002 mol) were then added and the mixture was stirred at room temperature overnight. The volatiles were removed and the residue was purified via flash column chromatography (120 g of silica gel, 0-50% EtOAc/Hexane) to give a yellow oil. MS m/z (M+H) 349.1.

Workup

  1. customconsumed
  2. temperaturethe reaction mixture was refluxed overnight
  3. customThe volatiles were removed via rotovapor
  4. customThe volatiles were removed
  5. customthe residue was purified via flash column chromatography (120 g of silica gel, 0-50% EtOAc/Hexane)
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-3c5b538a1dad488d92312dcd0adadbdd
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

Loading…