HCID 23316360, compound → HCID 23316354, compound

HRID 1982392Notes

Reaction equation

HRID 1982392 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[CH2:6][N:7]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]1[C:13]([O:15][CH3:16])=[O:14])([O-])=O>O1CCCC1.C(OCC)C.O.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:1][C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[CH2:6][N:7]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 1

HCID 23316360HCID 23316360, compound

Product 1

HCID 23316354HCID 23316354, compound

Reagents, catalysts & solvents 4

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2.68 g of methyl 1-(2-nitrobenzyl)-5-chloropyrrole-2-carboxylate in 30 mL of anhydrous tetrahydrofuran is added 35 mL of titanium trichloride in a dropwise manner over a 15 minute period. The reaction is allowed to stir at room temperature for 18 hours and then is diluted with 150 mL of a 1:1 mixture of diethyl ether and water. The organic phase is separated, washed with brine and saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and evaporated to dryness to yield methyl 1-(2-aminobenzyl)-5-chloropyrrole-2-carboxylate which is used in the next step without further purification.

Workup

  1. customThe organic phase is separated
  2. washwashed with brine and saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7a581f27bc5c42288412ab49003c348c
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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