Carbon Dioxide → HCID 12278957, compound

HRID 971486Notes

Reaction equation

HRID 971486 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1([Li])C=CC=CC=1.BrC1C=CC=CC=1.[Li].[Li][CH:27]1C2N=CC=CC=2CCC1.[C:37](=[O:39])=[O:38]>CCOCC>[CH3:27][O:38][C:37]([CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)=[O:39]

Participants

8

Reactant 6

HCID 280Carbon DioxideHCID 7961BromobenzeneHCID 663355,6,7,8-TetrahydroquinolineHCID 3028194LithiumHCID 178506676HCID 178506676, compoundHCID 178506835HCID 178506835, compound

Product 1

HCID 12278957HCID 12278957, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5,6,7,8-tetrahydroquinoline (14 g.) in dry ether (100 ml.) was added dropwise over 1/2 hour to an ethereal solution of phenyl lithium (prepared from bromobenzene (42 g.) and lithium (3.7 g.) in dry ether (300 ml.) and the reaction mixture stirred at room temperature for a further one hour. The cooled reaction mixture containing 8-lithio-5,6,7,8-tetrahydroquinoline was saturated with dry CO2 gas, evaporated in vacuo and the residue treated with methanol previously saturated with dry HCl (500 ml.) giving methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate as described in our copending U.S. Ser. No. 460,265.

Workup

  1. customThe cooled reaction mixture
  2. customevaporated in vacuo
  3. additionthe residue treated with methanol previously saturated with dry HCl (500 ml.)

Sources & evidence

ORD record
ord-683b73d089a24546a8c30887a6140537
Source dataset
uspto-grants-1979_07
Patent number
US04160094

Reaction notes

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