Hydrochloric Acid → HCID 178418234, compound

HRID 3658

Reaction equation

HRID 3658 reaction equation
[NH2:1][C:2]1C(CCC)C(=O)C(CCC)[C:4](=[O:15])[C:3]=1[NH:16][C:17]([CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=O.[OH-].[K+].Cl.[CH2:32]([OH:34])C>>[CH2:2]([N:1]1[C:4](=[O:15])[C:3]2[N:16]=[C:17]([CH:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[NH:1][C:2]=2[N:16]([CH2:17][CH2:19][CH3:20])[C:32]1=[O:34])[CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 700716701,2,3,4-Tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide

Product 1

HCID 178418234HCID 178418234, compound

Conditions

Temperature
70 °C

Procedure

Dissolve 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide (2.0 g, 5.2 mmol) in ethanol (50 ml), add 15% potassium hydroxide (50 ml) and heat to 70° C. for 4 hours. After cooling to 0° C., acidify the reaction with concentrated hydrochloric acid (13 ml). Add water (100 ml) and collect the resulting precipitate by suction filtration. Purify the white solid by flash chromatography (50% ethyl acetate/hexane) and triturate with 5% diethyl ether/hexane to provide, after drying under vacuum at 120° C. for 30 minutes the title compound (1.04 g), m.p. 202°-204° C.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customAdd water (100 ml) and collect the resulting precipitate
  3. filtrationby suction filtration
  4. customPurify the white solid by flash chromatography (50% ethyl acetate/hexane)
  5. customtriturate with 5% diethyl ether/hexane
  6. customto provide
  7. dry with materialafter drying under vacuum at 120° C. for 30 minutes the title compound (1.04 g), m.p. 202°-204° C.

Sources & evidence

ORD record
ord-08dfdae2443b4d4698992a68f3846a73
Source dataset
uspto-grants-1998_03
Patent number
US05734052

Linked notes

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