Hydrochloric Acid → HCID 70583694, compound

HRID 1448809Notes

Reaction equation

HRID 1448809 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH:13]=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10]1)=O)(C)(C)C.[OH-].[Na+].[ClH:21]>CO.O>[ClH:21].[NH2:8][CH:9]1[CH2:14][CH:13]=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20375726HCID 20375726, compound

Product 1

HCID 70583694HCID 70583694, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

1.4 g of methyl 3-(tert-butoxycarbonylamino)-1,5-cyclohexadienecarboxylate is treated with 164 mg of sodium hydroxide in 2 ml of methanol and 1 ml of water. The solution is stirred at about 25° C. for 3 hours, acidified to a pH of 3 with dilute hydrochloric acid and evaporated to dryness in vacuo. The residue is treated with 7 ml of methanol and 3.5 ml of 5% hydrochloric acid for 24 hours at 25° C. after which the solution is concentrated and washed with ether. The aqueous phase is evaporated in vacuo, and the residue is recrystallized from methanol-ether to afford 20 mg of 3-amino-1,5-cyclohexadiene carboxylic acid hydrochloride. M.P. 180°-184° C.

Workup

  1. customevaporated to dryness in vacuo
  2. additionThe residue is treated with 7 ml of methanol and 3.5 ml of 5% hydrochloric acid for 24 hours at 25° C. after which the solution
  3. concentrationis concentrated
  4. washwashed with ether
  5. customThe aqueous phase is evaporated in vacuo
  6. customthe residue is recrystallized from methanol-ether

Sources & evidence

ORD record
ord-fbe9febe4e124a5c992b6e22a440d696
Source dataset
uspto-grants-1980_02
Patent number
US04187316

Reaction notes

Loading…