Hydrochloric Acid → HCID 57736655, compound

HRID 2218709Notes

Reaction equation

HRID 2218709 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[CH:17]=[C:16]([CH:18]=[C:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][CH2:22][C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]2=3)[CH:15]=[CH:14][C:13]=1[OH:34].C([O-])(O)=O.[Na+].[OH-].[Na+].Cl>O.CO>[CH:29]1[C:24]2[CH2:23][CH2:22][C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[C:19](=[CH:18][C:16]3[CH:15]=[CH:14][C:13]4[O:34][C:2](=[O:3])[NH:11][C:12]=4[CH:17]=3)[C:25]=2[CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59770511HCID 59770511, compound

Product 1

HCID 57736655HCID 57736655, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add phenyl chloroformate (24 μL, 0.195 mmol) to a suspension of 2-amino-4-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenol (61 mg, 0.195 mmol) (see Example 63) and NaHCO3 (16 mg, 0.195 mmol) in water (5 mL) and methanol (10 mL). Stir for 30 min at room temperature and add aqueous NaOH (1.00N, 195□L). Stir overnight and add aqueous HCl (1.00N, 195□L). Extract with CH2Cl2, dry organics (MgSO4), and concentrate to a brown oil containing the title compound. Purify on silica gel (10 g) eluting with 10% TO 35% ethyl acetate/hexanes, and then triturate with 50% CH2Cl2/hexanes to afford 8 mg (13%) of a white solid. MS (ES) 357 (M+NH4), 338 (M−H); HPLC shows 94% purity.

Workup

  1. stirringStir overnight
  2. extractionExtract with CH2Cl2, dry organics (MgSO4)
  3. concentrationconcentrate to a brown oil
  4. additioncontaining the title compound
  5. customPurify on silica gel (10 g)
  6. washeluting with 10% TO 35% ethyl acetate/hexanes
  7. customtriturate with 50% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-854cc18e1ee6446199809a700cb08264
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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