Hydrochloric Acid → HCID 66653130, compound

HRID 535449Notes

Reaction equation

HRID 535449 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[C:6](C2C=CC=CC=2)=[C:7]([C:14]([C:16]2[CH:17]=[CH:18][C:19]3[N:24]=C(C4C=CC=CC=4)[O:22][C:21](=[O:31])[C:20]=3[CH:32]=2)=[O:15])[N:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]2.Cl>O.CN1CCCC1=O>[NH2:24][C:19]1[CH:18]=[CH:17][C:16]([C:14]([C:7]2[N:8]3[C:13]([CH:12]=[CH:11][CH:10]=[CH:9]3)=[C:5]([O:4][CH3:3])[CH:6]=2)=[O:15])=[CH:32][C:20]=1[C:21]([OH:31])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66653126HCID 66653126, compound

Product 1

HCID 66653130HCID 66653130, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

1.56 g (27.94 mmol) of potassium hydroxide dissolved in 4 ml of water are added, at ambient temperature, to 4.4 g (9.31 mmol) of 6-[(1-methoxy-2-phenylindolizin-3-yl)carbonyl]-2-phenyl-4H-3,1-benzoxazin-4-one in 50 ml of N-methylpyrrolidone. The reaction medium is heated at 80° C. for 24 hours. The reaction medium is poured into a 1N aqueous solution of hydrochloric acid. The precipitate formed is filtered off and rinsed with water. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 3.05 g of a green solid are obtained.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washrinsed with water
  4. customThe residue obtained
  5. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-6e9626754c514ca58f6b40b7218bc021
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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