Methylamine → HCID 118599718, compound

HRID 1054165Notes

Reaction equation

HRID 1054165 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6]/[C:7](=[CH:10]\[C:11](OCC)=[O:12])/[CH2:8][O:9][C:4]=2[CH:3]=1.[CH3:18][NH2:19]>CO>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6]/[C:7](=[CH:10]\[C:11]([NH:19][CH3:18])=[O:12])/[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 131736324HCID 131736324, compound2×

Product 1

HCID 118599718HCID 118599718, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of ethyl (2Z)-(7-fluoro-2H-1,4-benzoxazin-3(4H)-ylidene)acetate (Intermediate 11, 2.0 g; 8.4 mmol), MeOH (6.0 mL) and methylamine (7.3 mL of a 40 wt % aq. Solution, 84.3 mmol) was heated on a metal hotplate to 35° C. (block temperature) and stirred for 16 h. A dark brown cloudy solution was obtained. LCMS analysis indicated consumption of starting material and formation of product. The mixture was partitioned between DCM (80 mL) and water (80 mL). The organic phase was separated, then concentrated in vacuo and the residue purified by column chromatography on a 40 g silicycle silica cartridge eluting with 0-10% EtOAc: DCM, to obtain the title compound (1.10 g, 58.9%) of an orange crystalline solid that darkened on standing.

Workup

  1. customA dark brown cloudy solution was obtained
  2. customconsumption of starting material and formation of product
  3. customThe mixture was partitioned between DCM (80 mL) and water (80 mL)
  4. customThe organic phase was separated
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by column chromatography on a 40 g silicycle silica cartridge
  7. washeluting with 0-10% EtOAc

Sources & evidence

ORD record
ord-7e2adcfa1c264a518604b7a1b1b26061
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

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