Hydrochloric Acid → HCID 178422421, compound

HRID 1781236Notes

Reaction equation

HRID 1781236 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=[O:10])[C:3]=1[NH:12][C:13](=[O:18])[CH2:14]C(=O)C.[OH-].[Na+].Cl>C(O)(C)C.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]2[C:3]=1[N:12]=[C:13]([OH:18])[CH:14]=[N+:9]2[O-:10]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 19045060HCID 19045060, compound

Product 1

HCID 178422421HCID 178422421, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

The title compound of Step B (11.75 g, 37.29 mmol) was suspended in a mixture of isopropanol (120 mL) and water (120 mL) at room temperature under a nitrogen atmosphere. A solution of sodium hydroxide (14.91 g of a 50% aqueous solution, 186.4 mmol) diluted with water (10 mL) was added dropwise to the mixture over 30 min. The mixture was allowed to stir at room temperature overnight. First, 1N hydrochloric acid and then concentrated hydrochloric acid were added dropwise to the reaction mixture until the pH was approximately 2. Solids were filtered from the reaction mixture. These solids were washed with water and then cold ethyl acetate to afford the title compound of Step C as a reddish-brown solid melting at 241°-243° C. (8.67 g, 91%). 1H NMR ((CD3)2SO): δ2.47 (s,3H), 7.69 (s, 1H), 7.81 (s, 1H), 8.12 (s, 1H), 8.9 (br s, 1H).

Workup

  1. additionwas added dropwise to the mixture over 30 min
  2. filtrationSolids were filtered from the reaction mixture
  3. washThese solids were washed with water

Sources & evidence

ORD record
ord-961ef8e0d2254aeeb0222653c66e30f3
Source dataset
uspto-grants-1997_05
Patent number
US05633218

Reaction notes

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