Dimethylformamide → 3-benzyl-11-methoxy-1,2,4,5-tetrahydro-3H-azepino[4,5-b]quinoline

HRID 1288189Notes

Reaction equation

Cl.Cl.[CH2:3]([N:10]1[CH2:24][CH2:23][C:22]2[C:13](=[N:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:21]=2Cl)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C)[CH:28]=[O:29].C[O-].[Na+].[Na]>CO>[CH2:3]([N:10]1[CH2:24][CH2:23][C:22]2[C:13](=[N:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:21]=2[O:29][CH3:28])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

19.9 gm (50 millimols) of 3-benzyl-11-chloro-1,2,4,5-tetrahydro-3H-azepino[4,5-b]quinoline dihydrochloride and 500 ml of dimethyl formamide were added to dry sodium methylate, prepared from 23 gm of sodium and 1600 ml of methanol. The mixture was stirred at 100° C for 3 hours, evaporated, the residue was introduced into water, and the aqueous mixture was extracted with ether. The 3-benzyl-11-hydroxy-1,2,4,5-tetrahydro-3H-azepino[4,5-b]quinoline formed at the same time remained undissolved.

Workup

customevaporated
additionthe residue was introduced into water
extractionthe aqueous mixture was extracted with ether

Sources & evidence

ORD record: ord-a3844f2b596547d6888087f64eb3a40b
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03987047

Reaction notes

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