Methanol → HCID 57722728, compound

HRID 1986894Notes

Reaction equation

HRID 1986894 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[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=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[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=1[CH:23]=2)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 57722730HCID 57722730, compound

Product 1

HCID 57722728HCID 57722728, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
72 °C

Procedure

To a mixture of sodium hydride (95%) (0.70 g, 29 mmol, 2.6 equiv) in benzene (100 mL) at 23° C. under nitrogen was added methanol (2.5 mL, 2.0 g, 62 mmol, 5.4 equiv) dropwise over 10 min. After stirring for an additional 5 min, methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}-3-hydroxyprop-2-enoate (1-4) (4.1 g, 11 mmol, 1 equiv) was added and the resulting mixture was heated at 72° C. for 20 h. The solvent was evaporated under reduced pressure and the solid residue was suspended in water (50 mL) for 30 min followed by 1 N aqueous hydrochloric acid solution (100 mL) for an additional 30 min with stirring. The solid was filtered, washed with water (100 mL) and hexanes (100 mL), and dried to yield 3-acetyl-4-hydroxy-6,7,8,9-tetrahydrobenzo[g]quinolin-2(1H)-one (1-5) as an off-white solid. LRMS m/z (M+H) 258.4 found, 258.1 required.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. waitthe solid residue was suspended in water (50 mL) for 30 min
  3. waitfollowed by 1 N aqueous hydrochloric acid solution (100 mL) for an additional 30 min
  4. stirringwith stirring
  5. filtrationThe solid was filtered
  6. washwashed with water (100 mL) and hexanes (100 mL)
  7. customdried

Sources & evidence

ORD record
ord-fd77911f33d547f18b31d9e4f9e756ff
Source dataset
uspto-grants-2009_06
Patent number
US07550477B2

Reaction notes

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