Citric Acid → HCID 14032420, compound

HRID 246880Notes

Reaction equation

HRID 246880 reaction equation
C([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:7][C:6]([O:16]C(=O)C)=[CH:5]1)(=O)C.N#N.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[OH:16][C:6]1[CH:7]=[C:8]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[NH:4][CH:5]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 947NitrogenHCID 14798Sodium HydroxideHCID 13785343HCID 13785343, compound

Product 1

HCID 14032420HCID 14032420, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
-8 °C

Procedure

A sample of N-acetyl-3-acetoxyl-5p-chlorophenylpyrrole (16) (2.8 g; 0.01 mol) was deoxygenated for ten minutes with a stream of N2. The solids were then dissolved in deoxygenated methanol (30 mL) which was then chilled to -8° C. At once was added a cold deoxygenated solution of NaOH (1.6 g; 0.04 mol) in 20 mL H2O, which solution was then heated briefly to 15° C. and then immediately cooled to -5° C.; after 25 minutes the clear solution was treated with a cold deoxygenated solution of citric acid (4.2 g; 0.02 mol) in 15 mL H2O. The temperature rose briefly to 5° C. After 0.5 hr. stirring at -5° C., the solids were collected by filtration and washed with cold deoxygenated H2O. The pale green product was dried under vacuum at room temperature over P2O5 for several days (1.3 g; 68%); TLC Rf=0.19 (CHCl3 :EtOH, 9:1); IR (KCl) showed no evidence for C=O absorption.

Workup

  1. temperaturewas then heated briefly to 15° C.
  2. temperatureimmediately cooled to -5° C.
  3. customrose briefly to 5° C
  4. filtrationthe solids were collected by filtration
  5. washwashed
  6. customwith cold deoxygenated H2O
  7. dry with materialThe pale green product was dried under vacuum at room temperature over P2O5 for several days (1.3 g; 68%)
  8. customfor C=O absorption

Sources & evidence

ORD record
ord-02b274296a584cdc8a3f44bdc237d529
Source dataset
uspto-grants-1987_11
Patent number
US04704460

Reaction notes

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