4,N,N-Trimethylbenzamide → Isopropyl 3-p-toluoyl-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

HRID 648012Notes

Reaction equation

HRID 648012 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH2:9]C[CH2:7][CH2:6][N:5]2[CH:17]=1.CN(C)[C:20]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=[O:21]>>[C:25]1([CH3:28])[CH:26]=[CH:27][C:22]([C:20]([C:17]2[N:5]3[CH2:6][CH2:7][CH2:9][CH:10]([C:11]([O:13][CH:14]([CH3:15])[CH3:16])=[O:12])[C:4]3=[CH:3][C:2]=2[CH3:1])=[O:21])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 841794,N,N-TrimethylbenzamideHCID 20483821isopropyl 2-methyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-9-carboxylate

Product 1

HCID 20483828Isopropyl 3-p-toluoyl-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

Procedure

In like manner, condensing isopropyl 2-methyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-9-carboxylate with N,N-dimethyl-p-toluamide there is obtained isopropyl 5-p-toluoyl-2-methyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-1-carboxylate (XI, R=CH3, L=p-CHR=iC3H72, n=2).

Sources & evidence

ORD record
ord-939bc47b464c4773a786f10d5b456277
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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