Phosphorus sulfide (P2S5) → 2-Methyl-8-cyano-5,6,7,8-tetrahydroquinoline

Reaction equation

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

Participants

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)

HCID 122789682-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide

Product 1

HCID 203584122-Methyl-8-cyano-5,6,7,8-tetrahydroquinoline

Procedure

2-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide was treated with P2S5 to give 2-methyl-8-cyano-5,6,7,8-tetrahydroquinoline which was treated with H2S (both reactions being carried out by the method described in Example 8 to give the title compound as colourless needles from ethylacetate (28%) m.p. 98° (Found: C, 64.32; H, 6.93; N, 13.52%, C11H14N2S requires: C, 64.04; H, 6.84; N, 13.58%).

Sources & evidence

ORD record: ord-d31cdbac56204d39872d119c7d7b12f4
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04085215

Reaction notes

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