Hydrochloric Acid → HCID 53395370, compound

HRID 1669959Notes

Reaction equation

HRID 1669959 reaction equation
[N+:1]([CH:4]1[CH2:9][C:8]([CH:10]=O)=[CH:7][CH2:6][CH2:5]1)([O-:3])=[O:2].C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].Cl>N1C=CC=CC=1>[N+:1]([CH:4]1[CH2:9][C:8]([CH:10]=[CH:13][C:14]([OH:16])=[O:15])=[CH:7][CH2:6][CH2:5]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 575067495-Nitrocyclohex-1-ene-1-carbaldehyde

Product 1

HCID 53395370HCID 53395370, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-nitro-cyclohex-1-enecarbaldehyde (18 g, 0.116 mol) in pyridine (36 ml) was added malonic acid (41 g, 0.394 mol). The resulting suspension was heated to 60° C. for about 7 hours. After cooling to a temperature between 15° C. and 20° C., 6N HCl (72 ml) was slowly added into the reaction mixture to adjust the pH to between 1.5 and 2 while maintaining the temperature between 20° C. and 25° C. The mixture was then extracted with methylene chloride three times (1×180 ml, 2×90 ml). The combined extracts were washed with 1N HCl (48 ml), water (48 MI) and concentrated to a volume of 36 ml. The concentrate suspension was cooled to 0° C. and 5° C. for 1 hour. Light yellow solid was obtained after filtration and drying under vacuum. Yield: 10 g, 60%. Mp 158-160° C. 1HNMR (400 MHz, DMSO-d6): δ 2.10-2.33 (m, 4H), 2.73 (m, 2H), 4.96 (m, 1H), 5.83 (d, J=20 Hz, 1H), 6.28 (s, 1H), 7.27 (d, J=20 Hz, 1H), 12.3 (s, 1H).

Workup

  1. additionwas slowly added into the reaction mixture
  2. temperaturewhile maintaining the temperature between 20° C. and 25° C
  3. extractionThe mixture was then extracted with methylene chloride three times (1×180 ml, 2×90 ml)
  4. washThe combined extracts were washed with 1N HCl (48 ml), water (48 MI)
  5. concentrationconcentrated to a volume of 36 ml
  6. temperatureThe concentrate suspension was cooled to 0° C. and 5° C. for 1 hour
  7. customLight yellow solid was obtained
  8. filtrationafter filtration
  9. customdrying under vacuum

Sources & evidence

ORD record
ord-a973111596ec4d78b092ece83e0550b0
Source dataset
uspto-grants-2011_08
Patent number
US07989653B2

Reaction notes

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