Indomethacin → Allyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetate

HRID 542583

Reaction equation

[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC(C)=O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([N:10]2[C:9]3[C:4](=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=3)[C:3]([CH2:22][C:23]([O:25][CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[O:24])=[C:2]2[CH3:1])=[O:12])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

25 g of indometacin, 10 g of potassium carbonate and 1.0 g of benzyltriethylammonium chloride in 140 ml of acetone are stirred for 30 minutes at 50° to 60° C. 10.1 g of allyl chloroacetate are then added dropwise over 5 minutes. The mixture is stirred at 40° C. until the reaction has ended (as checked by thin layer chromatography; about 3 hours). The mixture is filtered while warm, the filtrate is evaporated in vacuo and the residue is taken up in ether (about 90 ml) and mixed with petroleum ether (40 to 60) (about 30 ml). This mixture is left to stand over night at -10° C. and the product is then filtered off and dried in vacuo.

Workup

custom(as checked by thin layer chromatography; about 3 hours)
filtrationThe mixture is filtered
temperaturewhile warm
customthe filtrate is evaporated in vacuo
additionmixed with petroleum ether (40 to 60) (about 30 ml)
waitThis mixture is left
waitto stand over night at -10° C.
filtrationthe product is then filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-3b0c8e80d6994da7b2c54c4961999ab1
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04658039

Linked notes

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