Hydrochloric Acid → HCID 44627146, compound

HRID 659051Notes

Reaction equation

HRID 659051 reaction equation
Cl.[CH2:2]([NH:5][C:6]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][N:9]1[C:17](=[O:33])[C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25]COC)=[CH:20][C:19]=1[O:29]COC)=[O:7])[CH:3]=[CH2:4].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:2]([NH:5][C:6]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][N:9]1[C:17](=[O:33])[C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([OH:25])=[CH:20][C:19]=1[OH:29])=[O:7])[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 44627260HCID 44627260, compound

Product 1

HCID 44627146HCID 44627146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride (4 mL, 16 mmol; 4 M in dioxane) was added to a solution of N-allyl-2-[5-chloro-2,4-bis(methoxymethoxy)benzoyl]isoindoline-1-carboxamide (392 mg, 0.85 mmol) in DCM (5 mL). The reaction was stirred at room temperature for 12 hours. The reaction mixture was neutralized with saturated NaHCO3 (aq) and then extracted with EtOAc (2×50 mL). The combined organic layers were dried, filtered, and evaporated to give the desired final product as the parent compound (N-allyl-2-(5-chloro-2,4-dihydroxybenzoyl)isoindoline-1-carboxamide) as a white solid (221 mg, 69.7% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.57 (d, J=79.33 Hz, 2 H), 4.65-4.93 (m, 1 H), 4.97-5.19 (m, 1 H), 5.42-5.70 (m, 1 H), 5.68-5.95 (m, 1 H), 6.40-6.71 (m, 1 H), 6.92 (s, 1 H), 7.15-7.67 (m, 4 H), 8.28 (s, 1 H), 10.06 (s, 1 H), 10.40 (s, 1 H). Anal. Calcd for C19H17ClN2O4: C, 61.21; H, 4.60; N, 7.51. Found: C, 61.02; H, 4.63; N, 7.36.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-62073c6f33164e9498862351f09e4e9d
Source dataset
uspto-grants-2011_12
Patent number
US08080556B2

Reaction notes

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