Water → HCID 85590048, compound

HRID 868155Notes

Reaction equation

HRID 868155 reaction equation
B(Br)(Br)Br.CC(C)(C)C([NH:9][NH:10][C:11]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][C:17]([O:25]C)=[C:18]([O:23]C)[CH:19]=2)[CH:14]=1)=[O:12])=O.O.CCOCC>ClCCl>[OH:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[OH:25])[CH:14]=[C:13]([C:11]([NH:10][NH2:9])=[O:12])[CH:22]=[CH:21]2

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 57319266HCID 57319266, compound

Product 1

HCID 85590048HCID 85590048, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -78° C., 3.5 g (14.2 mmol) of boron tribromide (0.5M in dichloromethane) was added dropwise to a solution of 1.59 g (4.7 mmol) of 6,7-dimethoxy-2-naphthalenecarboxylic acid, 2-(2,2-dimethyl-1-oxopropyl)hydrazide in 40 ml of dry dichloromethane. The solution was allowed to warm to room temperature and was stirred overnight. 30 ml of water and 115 ml of ether were added and the resulting precipitate filtered, washed and dried in vacuo to give 0.42 g of the title compound as its hydrobromide salt. The salt was dissolved in water and treated with one equivalent of sodium bicarbonate solution to give, after precipitation and collection by filtration, 0.22 g of the desired title compound.

Workup

  1. filtrationthe resulting precipitate filtered
  2. washwashed
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5a367dba25ce40dd8db2a619314c0325
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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