Hydrochloric Acid → HCID 68515557, compound

HRID 641961Notes

Reaction equation

HRID 641961 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:15]([OH:17])=[O:16])[C:5]2=[O:22].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH2:31][Cl:32].[OH-].[Na+].Cl>CN(C=O)C>[Cl:32][CH2:31][CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:15]([OH:17])=[O:16])[C:5]2=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 68511710HCID 68511710, compound

Product 1

HCID 68515557HCID 68515557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-(6-hydroxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoic acid (7.2 g) in DMF (150 ml) was added K2CO3 (33 g) and 1-bromo-2-chloroethane (12 ml) and heated to 50° C. for 2 hours. 2N NaOH (24 ml) was added and the solution heated to 40° C. for a further 16 hours. The pH was adjusted to pH˜1 with 1N HCl and the resultant solid collected by filtration. The solid was washed with methylene chloride, methanol and dried in vacuo to yield 3-[6-(2-chloroethoxy)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoic acid (9.1 g); NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 3.98 (m, 2H), 4.40 (m, 2H), 7.55 (m, 3H), 7.72 (d, 1H), 7.93 (s, 1H), 7.98 (d, 1H), 8.19 (s, 1H); Mass Spectrum: M+H+ 359.

Workup

  1. temperaturethe solution heated to 40° C. for a further 16 hours
  2. filtrationthe resultant solid collected by filtration
  3. washThe solid was washed with methylene chloride, methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c6dcd9e6c79c4074af04830fec88a101
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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