Hydrochloric Acid → HCID 135966567, compound

HRID 1073775Notes

Reaction equation

HRID 1073775 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:24])[C:5]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=2)=[C:6]([NH2:8])[N:7]=1.[OH-].[Na+].Cl>C(O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:24])[C:5]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 136068845HCID 136068845, compound

Product 1

HCID 135966567HCID 135966567, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Compound 1B (6.76 g, 20.3 mmoles) was treated with 300 mL of 1:1 ethanol/1.0N sodium hydroxide (V/V) and heated to 40° C. for 5 hours. The solution was treated with concentrated hydrochloric acid to pH 3.5, and the resulting solid was filtered and washed with 3 volumes (30 mL) of water. The solid was dissolved in 0.1N sodium hydroxide (355 mL) and treated dropwise with concentrated hydrochloric acid to pH 6.4 and filtered. The filtrate was further acidified to pH 3.5, refiltered, and the resulting solid was washed with 3 volumes (20 mL) of water and was dried at 50° C. in vacuo to yield 3.57 g (58%) of the title compound, 1C, as a white solid. Anal: Calcd for C14H16N4O4C, 55.26; H 5.29, N 18.41. Found: C 55.34; H, 5.31; N, 18.31. NMR (DMSO-d6) δ 1.8 (m, 2H, CH2 --CH2 --CH2), 2.3 (t, 2H, CH2 --CH2CH2 --O), 4.0 (t, 2H, CH2 --O), 5.7 (s, 2H, NH2), 5.9 (s, 2H, NH2), 9.8 (br s, ring NH), 12.6 (br, 1H, CO2H), 7.0 (d, 2H, benzoic H's ortho to oxygen), 7.85 (d, 2H, benzoic H's ortho to carbonyl). MS: (CI) 305 (M+1), 167 (M-OPhCO2H), 139 (H2OPhCO2H+).

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with 3 volumes (30 mL) of water
  3. dissolutionThe solid was dissolved in 0.1N sodium hydroxide (355 mL)
  4. additiontreated dropwise with concentrated hydrochloric acid to pH 6.4
  5. filtrationfiltered
  6. washthe resulting solid was washed with 3 volumes (20 mL) of water
  7. customwas dried at 50° C. in vacuo

Sources & evidence

ORD record
ord-306a9f70467a4acc801b9ed21284176b
Source dataset
uspto-grants-1990_11
Patent number
US04971973

Reaction notes

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