2-Amino-5-chlorobenzamide → HCID 178517743, compound

HRID 2225174Notes

Reaction equation

HRID 2225174 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:12]1([CH2:18][CH2:19][CH2:20][C:21](OC)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC[O-].[Na+].CC(O)=O.O>C(O)C>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:21]([CH2:20][CH2:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:6]=[C:4]2[OH:5]

Participants

6

Reactant 4

HCID 788762-Amino-5-chlorobenzamideHCID 281254Methyl 4-phenylbutyrateHCID 2723922Sodium ethoxideHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 178517743HCID 178517743, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

Preparation D8, Step 1: 2-Amino-5-chlorobenzamide (Avocado) (0.50 g, 2.93 mmol, 1 eq.), methyl 4-phenylbutyrate (3.14 g, 17.6 mmol, 6 eq.), NaOEt in ethanol (3.09 M, 5.69 mL, 17.6 mmol, 6 eq.) and ethanol (20 mL) were refluxed overnight. Cooled to 25° C. Added 10 mL of 10% HOAc/H2O. Solids formed which were filtered, the solids rinsed with 5 mL H2O, then dissolved in 20 mL of EtOAc/THF. Dried and stripped in vacuo followed by purification over silica gel in 3:1 to 1:1 Hexanes/EtOAc to give 6-chloro-2-(3-phenyl-propyl)-quinazolin-4-ol as a tan solid (200 mg). MS found: (M+H)+=299.

Workup

  1. customSolids formed which
  2. filtrationwere filtered
  3. washthe solids rinsed with 5 mL H2O
  4. dissolutiondissolved in 20 mL of EtOAc/THF
  5. customDried
  6. customfollowed by purification over silica gel in 3:1 to 1:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-1e8479c8debb4c45a9e476462a0ce72a
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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