Hydrochloric Acid → [6-(Acetylamino)-1-oxo-3,4-dihydro-2(1H)-naphthalenylidene]acetic acid

HRID 1242924Notes

Reaction equation

HRID 1242924 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[C:16]([OH:20])(=[O:19])[CH:17]=O.Cl>[OH-].[Na+]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[C:10](=[CH:17][C:16]([OH:20])=[O:19])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 54277852[6-(Acetylamino)-1-oxo-3,4-dihydro-2(1H)-naphthalenylidene]acetic acidYield 58.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.5N Aqueous sodium hydroxide solution (190 ml) was added to an aqueous solution(60 ml) of 6-acetamido-1-tetralone (5.00 g, 24.6 mmol) and glyoxylic acid (9.05 g, 98.5 mmol) under ice-cooling, which was stirred at 60 for 16 hours. After cooling, concentrated hydrochloric acid was added to the reaction mixture. The precipitated crystals were collected, which was washed with water, to give the titled compound (3.73 g).

Workup

  1. temperaturecooling
  2. temperatureAfter cooling
  3. customThe precipitated crystals were collected
  4. washwhich was washed with water

Sources & evidence

ORD record
ord-656b8ba3974e41148a08f3b366ef9b55
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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