Methylamine → HCID 59993125, compound

HRID 238214Notes

Reaction equation

HRID 238214 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([CH:11]([CH3:13])[CH3:12])[O:8][C:9](=O)[C:4]=2[CH:3]=1.[CH3:16][NH2:17]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:14][CH:15]=1)[N:6]=[C:7]([CH:11]([CH3:13])[CH3:12])[N:17]([CH3:16])[C:9]2=[O:8]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 59993318HCID 59993318, compound

Product 1

HCID 59993125HCID 59993125, compoundYield 33%

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-2-isopropyl-benzo[d][1,3]oxazin-4-one (2.75 g, 12.3 mmol) and methylamine (7.4 mL, 14.8 mmol, 2M solution in MeOH) were heated to 90° C. for 24 hours. The solvent was removed in vacuo and the residue was heated under reduced pressure to 160° C. for 2 hours. The reaction mixture was purified by column chromatography (0-30% ethyl acetate-hexanes) to yield the product (960 mg, 33%). 1H NMR H NMR (400 MHz, CDCl3) δ 8.23 (d, J=2.4 Hz, 1H), 7.65 (dd, J=8.7, 2.4 Hz, 1H), 7.61 (d, J=8.8 Hz, 1H), 3.69 (s, 3H), 3.22 (septet, J=6.7 Hz, 1H), 1.39 (d, J=6.7 Hz, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. temperaturethe residue was heated under reduced pressure to 160° C. for 2 hours
  3. customThe reaction mixture was purified by column chromatography (0-30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-280e871a1fde4b60a0647b77e6b2a8f1
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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