Hydrochloric Acid → HCID 13732846, compound

HRID 1731814Notes

Reaction equation

HRID 1731814 reaction equation
[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[C:15](=[O:16])[C:14]([C:17]([O:19]CC)=[O:18])=[CH:13][N:7]3[CH:8]([CH3:12])[CH2:9][O:10][C:11]=1[C:6]=23.Cl>O>[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[C:15](=[O:16])[C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:7]3[CH:8]([CH3:12])[CH2:9][O:10][C:11]=1[C:6]=23

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13732847HCID 13732847, compound

Product 1

HCID 13732846HCID 13732846, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 10-bromo-9-fluoro-3-methyl-7-oxo-2,3-dihydro-(7H)-pyrido-(1,2,3-de)-1,4-benzoxazine-6-carboxylate (0.2 g, 0.54 mmol) and a 3N hydrochloric acid solution (15 ml) were heated at 100° C. with stirring for 17 hours. The reaction mixture was diluted twofold with water and filtered. The white solid, which was collected, was washed with water, triturated with acetone, and filtered. Drying in vacuo afforded a white powder (142 mg, 77% yield): m.p. >250° C. NMR (5% DMSO-d6/CF3CO2D, 250 MHz): 9.12 (s, 1H), 7.80 (d, 1H, J=8 Hz), 5.10-5.00 (m, 1 H), 4.80-4.70 (m, 1H), 4.60-4.50 (m, 1H), 1.52 (d,3H, J=7 Hz).

Workup

  1. filtrationfiltered
  2. customThe white solid, which was collected
  3. washwas washed with water
  4. customtriturated with acetone
  5. filtrationfiltered
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-946438d264cb4ec8aa76376d3305fcd6
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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