Hydroxide → 2-Hydroxy-5-((3,5-bis(methoxycarbonyl)phenyl)azo)benzeneacetic acid

HRID 4419

Reaction equation

HRID 4419 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)=[O:4].[N:16]([O-])=O.[Na+].[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28]([OH:30])=[O:29].[OH-]>Cl.O.[OH-].[Na+].C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([N:11]=[N:16][C:24]2[CH:25]=[CH:26][C:21]([OH:20])=[C:22]([CH2:27][C:28]([OH:30])=[O:29])[CH:23]=2)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)=[O:4]

Participants

9

Reactant 4

HCID 961HydroxideHCID 11970(2-Hydroxyphenyl)acetic acidHCID 66831Dimethyl 5-aminoisophthalateHCID 23668193Sodium Nitrite

Product 1

HCID 1273242-Hydroxy-5-((3,5-bis(methoxycarbonyl)phenyl)azo)benzeneacetic acid

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

20.9 g of dimethyl-5-amino-benzene-1,3-dicarboxylate was dissolved in 20 ml of concentrated hydrochloric acid in 200 ml of ice water. The solution was diazotized with 7 g of sodium nitrite dissolved in 30 ml of water. 30.4 g of 2-hydroxy-phenylacetic acid was dissolved in 200 ml of water and 24 g of sodium hydroxide. The solution was cooled with 100 g of ice. To this hydroxide solution was then added the diazonium salt solution, all at once, and with vigorous stirring. After 30 seconds the solution was acidified with acetic acid and the precipitate was filtered off. The precipitate was leached with an about 25% ethanol solution which was then diluted with water until a state of weak opalescence was reached. The solution was treated with active carbon and evaporated down to half its volume. Sodium hydrogen carbonate was added until the solution was clear, whereupon the solution was heated (80° C.) and acidified with hydrochloric acid. The solution was cooled, the crystals were filtered off and dried.

Workup

  1. filtrationthe precipitate was filtered off
  2. additionwas then diluted with water until a state of weak opalescence
  3. additionThe solution was treated with active carbon
  4. customevaporated down to half its volume
  5. additionSodium hydrogen carbonate was added until the solution
  6. temperatureThe solution was cooled
  7. filtrationthe crystals were filtered off
  8. customdried

Sources & evidence

ORD record
ord-8f9ba23024a24c68b03865b18a945605
Source dataset
uspto-grants-1988_02
Patent number
US04725676

Linked notes

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