Hydrochloric Acid → HCID 21406505, compound

HRID 1729898Notes

Reaction equation

HRID 1729898 reaction equation
C[C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10](N)[CH:11]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18].Cl.N([O-])=[O:22].[Na+].S(=O)(=O)(O)O>O>[OH:22][C:9]1[CH:8]=[C:7]2[C:12]([C:13]3[CH:5]=[CH:4][C:3]([CH2:16][C:17]([OH:19])=[O:18])=[CH:2][C:14]=3[CH2:6]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 70633535HCID 70633535, compound

Product 1

HCID 21406505HCID 21406505, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 14.5g. of methyl 7-aminofluorene-2-acetic acid in 380ml. of water containing 14ml. of concentrated hydrochloric acid is cooled to 2° and a solution of 3.63g. of sodium nitrite in 15ml. of water added dropwise while stirring. The diazonium solution is added over a 1 hour period while stirring to a refluxing solution of 1.1 liters of water containing 18ml. of sulfuric acid. The mixture is cooled and the solid collected by filtration. The solid is refluxed with 120ml. of 10% aqueous potassium hydroxide solution for 2 hr., and treated with Darco. The suspension is filtered, acidified with hydrochloric acid and the solid collected by filtration, dried, and crystallized from acetonitrile to give 9.4g. of the title compound, 240°-241°d.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe solid collected by filtration
  3. temperatureThe solid is refluxed with 120ml
  4. addition, and treated with Darco
  5. filtrationThe suspension is filtered
  6. filtrationthe solid collected by filtration
  7. customdried
  8. customcrystallized from acetonitrile
  9. customto give 9.4g

Sources & evidence

ORD record
ord-707ad788e523456aa19660c732288290
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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