2-Amino-5-bromobenzoic acid → HCID 178517953, compound

HRID 2225181Notes

Reaction equation

HRID 2225181 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[CH:16](N)=[NH:17]>C(OCCO)C.C(OCC)C>[Br:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:16][N:17]=[C:4]2[OH:5]

Participants

5

Reactant 2

HCID 798582-Amino-5-bromobenzoic acidHCID 160693Formamidine acetate

Product 1

HCID 178517953HCID 178517953, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

Preparation D12, Step 1: A mixture of 2-amino-5-bromobenzoic acid (5.7 g, 24.78 mmol) and formamidine acetate (5.2 g, 49.5 mmol) in 2-ethoxyethanol (50 mL) was heated at reflux for 4 h. The reaction was cooled to room temperature, allowed to stand overnight, then diluted with diethyl ether (20 mL) to further precipitate the product. The solids were collected by filtration, rinsed with 2-ethoxyethanol (10 mL), diethyl ether (2×50 mL), and air dried to yield 4.4 g of 6-bromoquinazolin-4-ol as a tan solid. MS (ES+)=225/227 (M+H+).

Workup

  1. customPreparation D12, Step 1
  2. temperaturewas heated
  3. temperatureat reflux for 4 h
  4. filtrationThe solids were collected by filtration
  5. washrinsed with 2-ethoxyethanol (10 mL), diethyl ether (2×50 mL), and air
  6. customdried

Sources & evidence

ORD record
ord-76df37fd604a434aba7abd2a5f8d29f9
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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