Ethyl Acetate → HCID 178422923, compound

HRID 1672485Notes

Reaction equation

HRID 1672485 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[C:12]([O:20][CH2:21][C:22]([O:24]C)=[O:23])[C:13]([CH3:19])=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1.[OH-].[Na+].CCOC(C)=O>CO>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[C:12]([O:20][CH2:21][C:22]([OH:24])=[O:23])[C:13]([CH3:19])=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178501760HCID 178501760, compound

Product 1

HCID 178422923HCID 178422923, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl ({2-[(trans-4-hydroxycyclohexyl)amino]-7-methylquinazolin-8-yl}oxy)acetate (11 g, 0.032 mol) in MeOH (210 mL) was added 2 N aq. NaOH (81.4 mL, 0.163 mol) in one portion. The reaction mixture was stirred at room temperature overnight. TLC (EtOAc) indicated the reaction was complete. The solvent was removed in vacuo. The residue was adjusted to pH 6 with 1 N aq. HCl. The precipitate was filtered, washed with ether (30 mL×2) and dried in vacuo to give the title compound (9.8 g, 92.4%) as an off-white solid. m/e 332.2 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationThe precipitate was filtered
  3. washwashed with ether (30 mL×2)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-75166ea0fec341368f1ce127a0283a72
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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