Benzoyl chloride → HCID 21313377, compound

HRID 2397495Notes

Reaction equation

HRID 2397495 reaction equation
COC1C=CC(NN)=CC=1.O=C(CCC)C(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].OCCC1C2C(=CC=C(OC)C=2)NC=1C.[H-].[Na+].[Na].C(Cl)(=O)C1C=CC=CC=1.[C:54]([N:62]1[C:70]2[C:65](=[CH:66][C:67]([O:71][CH3:72])=[CH:68][CH:69]=2)[C:64]([CH2:73][CH2:74]O)=[C:63]1[CH3:76])(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.S(Br)([Br:79])=O.C(=O)([O-])[O-].[Ca+2]>C(O)C.O1CCCC1.CN(C=O)C.C1C=CC=CC=1>[C:54]([N:62]1[C:70]2[C:65](=[CH:66][C:67]([O:71][CH3:72])=[CH:68][CH:69]=2)[C:64]([CH2:73][CH2:74][Br:79])=[C:63]1[CH3:76])(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

15

Reactant 10

HCID 7412Benzoyl chlorideHCID 10112Calcium CarbonateHCID 24758Sodium hydrideHCID 68176Thionyl bromideHCID 77023(4-Methoxyphenyl)hydrazineHCID 123521Ethyl 2-oxovalerateHCID 5360545SodiumHCID 11447063HCID 11447063, compoundHCID 21226445Aluminium lithium hydrideHCID 21313402HCID 21313402, compound

Product 1

HCID 21313377HCID 21313377, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 4-methoxyphenylhydrazine with ethyl α-ketovalerate in ethanol using the procedure described above in Example 1; reduction with lithium aluminum hydride in tetrahydrofuran of the resulting ethyl α-(5-methoxy-2-methyl-3-indole)-acetate; reaction of the resulting 3-(2-hydroxyethyl)-5-methoxy-2-methylindole with sodium hydride in DMF, and reaction of the resulting sodium salt with benzoyl chloride using the procedure described above in Example 1; and reaction of the resulting 1-benzoyl-3-(2-hydroxyethyl)-5-methoxy-2-methylindole with thionyl bromide in benzene in the presence of calcium carbonate using the procedure described in U.S. Pat. No. 3,517,028 affords 1-benzoyl-3-(2-bromoethyl)-5-methoxy-2-methylindole. The latter, on reaction with an appropriate amine in refluxing acetone in the presence of sodium carbonate affords the compounds of formula I in Examples 72-77 below where, in each instance, R1 is 5-CH3O; R2 is CH3 ; A is C6H5CO; and Alk is CH2CH2.

Sources & evidence

ORD record
ord-f814d5cc1bdf4b07977adc2ecd43a9bd
Source dataset
uspto-grants-1977_05
Patent number
US04021431

Reaction notes

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