Sodium → 6-Bromo-2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol

HRID 1829777Notes

Reaction equation

HRID 1829777 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[Br:25])C1C=CC=CC=1.[Na]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:25][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[C:15]([CH3:19])[CH:14]=[C:13]2[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 220545387-Benzyloxy-6-bromo-2-methyl-4-pyrrolidin-1-yl-quinoline

Product 1

HCID 1358041206-Bromo-2-methyl-4-pyrrolidin-1-yl-quinolin-7-olYield 63.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 7-benzyloxy-6-bromo-2-methyl-4-pyrrolidin-1-yl-quinoline (2.3 g, 5.79 mmol) in dichloromethane (70 mL) was added a 1M solution of titanium tetrachloride in dichloromethane (48.6 mL, 48.6 mmol) within 20 min. After 1h, the reaction mixture was poured onto an aqueous solution of sodium hydrogenocarbonate, extracted with dichloromethane and evaporated. 1.13 g of the title compound was obtained. Yellow solid, ISP-MS: m/e=308.1 ([M+H]+).

Workup

  1. extractionextracted with dichloromethane
  2. customevaporated

Sources & evidence

ORD record
ord-9f0205e7d8b84749a3d8afd28424c62a
Source dataset
uspto-grants-2006_06
Patent number
US07064134B2

Reaction notes

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