Methanol → HCID 57559684, compound

HRID 1723831Notes

Reaction equation

HRID 1723831 reaction equation
[H-].[Na+].CO.[C:5](/[C:8](=[C:13](\[C:15]1[C:24]([NH:25][C:26]([O:28]CC)=O)=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)/[OH:14])/C(OC)=O)(=[O:7])[CH3:6]>C1C=CC=CC=1>[C:5]([C:8]1[C:26](=[O:28])[NH:25][C:24]2[C:15]([C:13]=1[OH:14])=[CH:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=1[CH:23]=2)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 57559686HCID 57559686, compound

Product 1

HCID 57559684HCID 57559684, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
72 °C

Procedure

To a dispersion of sodium hydride (95%) (0.90 g, 37.5 mmol, 2.6 equiv) in benzene (100 ml) at room temperature under nitrogen was added dropwise methanol (3.0 ml, 2.37 g, 74.1 mmol, 5.2 equiv). After stirring for 5 minutes, methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-2-naphthyl}-3-hydroxyprop-2-enoate (1-3) (5.06 g, 14.2 mmol, 1.0 equiv) was added and the reaction was heated to 72° C. for 20 hours. The solvent was evaporated under reduced pressure and the solid residue was stirred with water (50 ml) for 30 minutes followed by 1 N HCl (100 ml) for an additional 30 minutes. The solid was filtered, washed with water (100 ml) and hexanes (100 ml) and dried to yield 3-acetyl-4-hydroxybenzo[g]quinolin-2(1H)-one (1-4) as a yellow solid. LRMS m/z (M+H) 254.2 found, 254.1 required.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. stirringthe solid residue was stirred with water (50 ml) for 30 minutes
  3. waitfollowed by 1 N HCl (100 ml) for an additional 30 minutes
  4. filtrationThe solid was filtered
  5. washwashed with water (100 ml) and hexanes (100 ml)
  6. customdried

Sources & evidence

ORD record
ord-e79bc011179a4ec085006a25ef69a2f1
Source dataset
uspto-grants-2009_02
Patent number
US07485649B2

Reaction notes

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