Trifluoroacetic acid → 6-Fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

HRID 1271053Notes

Reaction equation

HRID 1271053 reaction equation
COC1C=CC(C[N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[C:16]([F:21])[C:17]([NH:19][CH3:20])=[CH:18][C:11]=3[O:10][CH2:9]2)=CC=1.FC(F)(F)C(O)=O>>[F:21][C:16]1[C:17]([NH:19][CH3:20])=[CH:18][C:11]2[O:10][CH2:9][NH:8][C:13](=[O:14])[C:12]=2[CH:15]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 184524883-(4-Methoxybenzyl)6-fluoro-7-(methylamino)2,3-dihydrobenzo[e][1,3]oxazin-4-one

Product 1

HCID 184525146-Fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-oneYield 72.8%

Procedure

To 3-(4-methoxybenzyl)6-fluoro-7-(methylamino)2,3-dihydrobenzo[e][1,3]oxazin-4-one (1 g, 3.5 mmol) added trifluoroacetic acid ((5 mL) and heated the reaction at 80° C. for 4 hr. RP-HPLC showed formation of new peak and disappearance of SM peak. The trifluoroacetic acid was removed under vacuum and the residue suspended in ethyl acetate and washed with saturated sodium bicarbonate solution. The ethyl acetate was dried, filtered and evaporated to afford 6-Fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one as off-white solid (0.500 g, 72%) after triturating with diethyl ether. RP-HPLC: 1.58 min; ES-MS (M+H)+=198.0; 1H-NMR (CDCl3) δ (ppm): 7.5 (d, 1), 6.4 (s, 1), 6.15 (d, 1), 5.17 (s, 2), 2.91 (s, 3)

Workup

  1. temperatureheated
  2. customthe reaction at 80° C. for 4 hr
  3. customThe trifluoroacetic acid was removed under vacuum
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialThe ethyl acetate was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-46526f16afd346c8b1b7d3483b2dca30
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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