Ammonia → HCID 68279452, compound

HRID 525423Notes

Reaction equation

HRID 525423 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[CH:17]=O)=O)(=O)C.[NH3:19]>CCO>[CH3:16][O:15][C:12]1[CH:11]=[C:10]2[C:9](=[CH:14][CH:13]=1)[N:8]=[C:6]([CH2:5][OH:4])[N:19]=[CH:17]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 88920476HCID 88920476, compound

Product 1

HCID 68279452HCID 68279452, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of 2-(2-formyl-4-methoxyphenylamino)-2-oxoethyl acetate (5 g, 0.02 mol) and ammonia (6.8 g, 0.4 mol, 20 eq) in EtOH (30 mL) was reacted under a high pressure (30 psi) at 135° C. for 5 h. After cooling to room temperature, the solvent was evaporated in vacuum. The residual aqueous solution was extracted with DCM (100 mL×3). The combined extracts were dried over anhydrous Na2SO4 and evaporated to dryness in vacuum. The crude product was purified by chromatography (eluting with DCM/MeOH=100/1) to give (6-methoxyquinazolin-2-yl)methanol (4.1 g, yield: 90%) as a white solid. 1HNMR (400 MHz, DMSO-d6) δ: 9.46 (s, 1H), 7.90 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.8, 3.2 Hz, 1H), 7.52 (d, J=2.8 Hz, 1H), 5.34 (t, J=6.4 Hz, 1H), 4.72 (d, J=6.4 Hz, 2H), 3.91 (m, 3H); ESI-MS: m/z 191.1 ([M+1]+).

Workup

  1. customthe solvent was evaporated in vacuum
  2. extractionThe residual aqueous solution was extracted with DCM (100 mL×3)
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. customevaporated to dryness in vacuum
  5. customThe crude product was purified by chromatography (eluting with DCM/MeOH=100/1)

Sources & evidence

ORD record
ord-5b90a5ed7bf742d89f255d5fab17f007
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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