Citric Acid → HCID 14032420, compound

HRID 623261Notes

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

Conditions

Temperature: -8 °C

Procedure

A sample of N-acetyl-3-acetoxy-5-p-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

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

Sources & evidence

ORD record: ord-f0c45c6df2074f5ea56eb1d1d8ed5287
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04774340

Reaction notes

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