Hydrochloric Acid → HCID 178487715, compound

HRID 1925366Notes

Reaction equation

HRID 1925366 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[CH3:13]C([O-])(C)C.[Na+].C(OCC)=O.Cl>O1CCOCC1.O>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:10]([OH:12])=[CH:11][CH:13]=[N:1]2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 106786151-(2-Amino-4-methoxyphenyl)ethan-1-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 178487715HCID 178487715, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-(2-amino-4-methoxyphenyl)ethanone [J Med Chem, 32(4):807-826 (1989)] (7.32 g, 44.3 mmol) in dioxane (150 mL), NaOt-Bu (9.8 g, 102 mmol) was added and stirred at RT for 30 min. The color changed from lime green to dark green. Ethyl formate (23.64 mL, 292 mmol) was added with an additional 20 mL dioxane. The reaction mixture was stirred at RT 18 h after which the mixture was poured into water (20 mL) and the pH adjusted to 7 with 2N HCl. The solution was evaporated a little. The red solid was filtered and rinsed with water. The solid was triturated with 1:1 EtOAc:hexanes and then filtered to give the title compound as a brown solid.

Workup

  1. stirringThe reaction mixture was stirred at RT 18 h after which the mixture
  2. customThe solution was evaporated a little
  3. filtrationThe red solid was filtered
  4. washrinsed with water
  5. customThe solid was triturated with 1:1 EtOAc
  6. filtrationhexanes and then filtered

Sources & evidence

ORD record
ord-e83f07fdc98e4d8c81e05ae6f50ddd31
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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