Hydrochloric Acid → 2-Amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acid

HRID 1502209Notes

Reaction equation

HRID 1502209 reaction equation
[Br:1][C:2]1[C:3]([CH3:31])=[C:4]([C:11](/[C:13](=[CH:29]/[CH3:30])/[CH:14]=[C:15]2\[C:16](=C)[N:17]=C(C3C=CC=CC=3)[O:19][C:20]\2=[O:21])=[O:12])[N:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.[OH-].[K+].Cl>O.CN1C(=O)CCC1>[NH2:17][C:16]1[CH:30]=[CH:29][C:13]([C:11]([C:4]2[N:5]3[C:10]([CH:9]=[CH:8][CH:7]=[CH:6]3)=[C:2]([Br:1])[C:3]=2[CH3:31])=[O:12])=[CH:14][C:15]=1[C:20]([OH:19])=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 117761369(5E)-5-{(2E)-2-[(1-bromo-2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-4-methylidene-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-one

Product 1

HCID 666531732-Amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acidYield 109.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The (5E)-5-{(2E)-2-[(1-bromo-2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-4-methylidene-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-one (18.6 g; 40.4 mmol) is added portionwise to potassium hydroxide (22.7 g; 0.40 mol) in 100 mL of water and 140 mL of NMP. The reaction mixture is heated at reflux for 18 h, cooled to ambient temperature and poured into a hydrochloric acid solution (1 M). The yellow precipitate formed is filtered off and dried under vacuum to give 16.5 g (99%) of a yellow powder.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 18 h
  3. customThe yellow precipitate formed
  4. filtrationis filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7ba755a81a094572a9e825f06db68e24
Source dataset
uspto-grants-2015_12
Patent number
US09206177B2

Reaction notes

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