Sulfuric Acid → HCID 59455127, compound

HRID 1401469Notes

Reaction equation

HRID 1401469 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)(O)[CH3:13])[C:6]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:5]=3[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](/[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)\[CH3:13])[C:6]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 57876294HCID 57876294, compound

Product 1

HCID 59455127HCID 59455127, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
7.5 °C

Procedure

1-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-2-(4-methoxyphenyl)propan-2-ol (500 mg, 1.3 mmol, 1 equiv.) was heated to 55° C. with sulfuric acid (0.375 mL) in water (5 mL) for 2.5 h, cooled to 5-10° C. and neutralized by dropwise addition of saturated aqueous sodium hydrogen carbonate solution followed by extraction with EtOAc (2×15 mL). The combined organic extract was washed with water (10 mL), brine, dried over sodium sulfate and evaporated under reduced pressure to obtain 330 mg of product. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 7.60 (m, 3H), 7.24 (d, 1H), 7.19 (d, 1H), 7.10 (d, 1H), 7.0 (m, 2H), 4.40 (m, 2H), 3.80 (s, 3H), 3.10 (m, 4H), 2.80 (s, 3H), 1.80 (s, 3H).

Workup

  1. extractionfollowed by extraction with EtOAc (2×15 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water (10 mL), brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-540c5c9beb124450ae5927f0bbcf5d4b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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