Phosphorus sulfide (P2S5) → 8-Cyano-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 2083213Notes

Reaction equation

HRID 2083213 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]([NH2:14])=O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]#[N:14])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 122782273-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide

Product 1

HCID 122782108-Cyano-3-methyl-5,6,7,8-tetrahydroquinoline

Procedure

3-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide was treated with P2S5 to give 3-methyl-8-cyano-5,6,7,8-tetrahydroquinoline which was treated with H2S as described in Example 8 giving the title compound as colourless needles from benzene m.p. 151° (50% yield) (Found: C, 63.71; H, 6.85; N, 13.38% C11H14N2S requires: C, 64.94; H, 6.84; H, 13.58%).

Sources & evidence

ORD record
ord-bc7be191a906477297e09beeef41ed6a
Source dataset
uspto-grants-1978_04
Patent number
US04085110

Reaction notes

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