Hydrochloric Acid → HCID 9860275, compound

HRID 1071193Notes

Reaction equation

HRID 1071193 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH:10]([CH2:15][C:16]#N)[CH2:9][CH2:8]2)(=O)C.[CH2:18]([OH:20])[CH3:19].CC[O:23]CC.C(O)(C)C.[ClH:30]>>[ClH:30].[NH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH:10]([CH2:15][C:16]([O:20][CH2:18][CH3:19])=[O:23])[CH2:9][CH2:8]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22147583Diethyl ether 2-propanolHCID 22471904HCID 22471904, compound

Product 1

HCID 9860275HCID 9860275, compoundYield 80%

Procedure

A mixture of 1.5 g of 6-acetamido-2-cyanomethylchromane (Example 14) in 25 mL of concentrated hydrochloric acid is stirred vigorously at room temperature for about 6 h. Ethanol (50 mL) is added and the mixture allowed to stand overnight. The precipitate is filtered, rinsed with 50-mL aliquots of ether, and dried. Absolute ethanol (25 mL) and HCl (10 mL) are stirred with the precipitate for 2 h, followed by addition of 10 mL of concentrated HCl. The precipitate is recovered and recrystallized twice from ether/isopropanol affording about 1.3 g of ethyl 2-(6-aminochroman-2-yl)acetate hydrochloride (about 80% yield).

Workup

  1. waitto stand overnight
  2. filtrationThe precipitate is filtered
  3. washrinsed with 50-mL aliquots of ether
  4. customdried
  5. stirringAbsolute ethanol (25 mL) and HCl (10 mL) are stirred with the precipitate for 2 h
  6. additionfollowed by addition of 10 mL of concentrated HCl
  7. customThe precipitate is recovered

Sources & evidence

ORD record
ord-619c27d75542464bb6ba44d3b5e813a5
Source dataset
uspto-grants-2005_06
Patent number
US06903227B2

Reaction notes

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