Hydrochloric Acid → HCID 90332433, compound

HRID 595591Notes

Reaction equation

HRID 595591 reaction equation
[NH2:1][C:2]1[C:18]([Br:19])=[CH:17][C:5]2[C:6]([C:12]([O:14]CC)=[O:13])=[C:7]([CH:9]3[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.O[Li].O.Cl>O1CCOCC1.O>[NH2:1][C:2]1[C:18]([Br:19])=[CH:17][C:5]2[C:6]([C:12]([OH:14])=[O:13])=[C:7]([CH:9]3[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 90332507HCID 90332507, compound

Product 1

HCID 90332433HCID 90332433, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 6-amino-5-bromo-2-cyclopropylbenzofuran-3-carboxylate (7 g, 22.5 mmol) in 1,4-dioxane and H2O (50 mL and 50 mL) was added LiOH.H2O (4.6 g, 112 mmol). The reaction mixture was refluxed for 2 hours, and then 400 mL H2O was added to the reaction mixture. After acidifying to pH 4˜5 with HCl, the resulting solid were filtered to give the product of 6-amino-5-bromo-2-cyclopropylbenzofuran-3-carboxylic acid (6.5 g, yield: 97%). 1H-NMR (400 MHz, MeOD) δ 7.86 (s, 1H), 6.85 (s, 1H), 4.31 (s, 2H), 2.93˜3.00 (m, 1H), 1.19˜1.22 (m, 2H), 1.13˜1.16 (m, 2H). MS (M+H)+: 296/298.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. filtrationthe resulting solid were filtered

Sources & evidence

ORD record
ord-84aa311212fe40abb668a6a60163cb35
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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