Hydrochloric Acid → Ethyl 2,4-dihydroxy-5,6,7,8-tetrahydroquinazoline-6-carboxylate

HRID 22004Notes

Reaction equation

HRID 22004 reaction equation
[C:1]([C:6]1(C(OCC)=O)[CH2:15][CH2:14][C:13]2[NH:12][C:11](=[O:16])[NH:10][C:9](=[O:17])[C:8]=2[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].Cl>[OH-].[Na+]>[C:1]([CH:6]1[CH2:15][CH2:14][C:13]2[NH:12][C:11](=[O:16])[NH:10][C:9](=[O:17])[C:8]=2[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 152840896,6-Dicarboethoxy-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 15284090Ethyl 2,4-dihydroxy-5,6,7,8-tetrahydroquinazoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of of 6,6-Dicarboethoxy-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione (25 g) in 1N NaOH (350 mL) was stirred at 40° C. for 35 min. The solution was cooled in an ice bath and acidified with 35 mL of concentrated HCl. The precipitate that formed was collected and refluxed in 20 ml of dimethylformamide (DMF) for 2 h. The reaction was cooled and the DMF removed in vacuo. To the resulting mixture 40 mL of water was added and the solid collected and dried to yield 6-Carboethoxy-5,6,7,8-tetrahydro-2,4(1H ,3H)-quinazolinedione.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe precipitate that formed
  3. customwas collected
  4. temperaturerefluxed in 20 ml of dimethylformamide (DMF) for 2 h
  5. temperatureThe reaction was cooled
  6. customthe DMF removed in vacuo
  7. additionTo the resulting mixture 40 mL of water was added
  8. customthe solid collected
  9. customdried

Sources & evidence

ORD record
ord-2c4acd62b4744dfea4477d58c9a032b0
Source dataset
uspto-grants-1995_06
Patent number
US05426186

Reaction notes

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