Methylamine → HCID 57983409, compound

HRID 2078313Notes

Reaction equation

HRID 2078313 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15](OCC)=[O:16])=[C:5]2[OH:20].C1COCC1.[CH3:26][NH2:27]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:27][CH3:26])=[O:16])=[C:5]2[OH:20]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 67099655HCID 67099655, compound

Product 1

HCID 57983409HCID 57983409, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (1.10 g, 3732 μmol, see Example 2) was dissolved in 2M methanamine in THF (9331 μL, 18661 μmol). The resulting mixture was stirred at 60° C. for 16 hours and then diluted with 100 mL of EtOAc. The resulting mixture was added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 20 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4 and concentrated in vacuo to give the title compound (131 mg) as a white solid after purification via preparatory LC. MS m/e=280 (M+H)+. Calculated for C14H14ClNO3 279.07.

Workup

  1. additionThe resulting mixture was added to a separatory funnel
  2. custompartitioned with NaHCO3 (saturated, aqueous)
  3. washwashed 2 times with 20 mL of NaHCO3 (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60b0a19ee6d54ee4aa2331ff3571761b
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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