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

HRID 1743938Notes

Reaction equation

HRID 1743938 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 1 h, 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-6cec9e2737ad44d08208feeb21c757ac
Source dataset
uspto-grants-2006_03
Patent number
US07012073B2

Reaction notes

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