Phenol → Benzo[g]quinazoline-2,4(1H,3H)-dione

HRID 1783769Notes

Reaction equation

HRID 1783769 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:15][C:16](N)=[O:17].C1(O)C=CC=CC=1>>[NH:1]1[C:2]2[C:3](=[CH:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:11]=2)[C:12](=[O:14])[NH:15][C:16]1=[O:17]

Participants

4

Reactant 3

HCID 996PhenolHCID 1176UreaHCID 222443-Amino-2-naphthoic acid

Product 1

HCID 611366Benzo[g]quinazoline-2,4(1H,3H)-dione

Conditions

Temperature
185 °C

Procedure

A mixture of 3-amino-2-naphthoic acid (8-1,1.2 g, 6.6 mmol, 1 equiv), urea (2.0 g, 33 mmol, 5.0 equiv) and phenol (7.0 g, 74 mmol, 11 equiv) was heated at 160° C. for 0.5 h an 185° C. for an additional 1.5 h. The reaction was cooled and triturated with methanol (50 mL). The solid precipitate was filtered, washed with methanol, and dried to yield benzo[g]quinazoline-2,4(1H,3H)-dione (1-2) as an orange solid. LRMS m/z (M+H) 213.1 found, 213.1 required.

Workup

  1. temperatureThe reaction was cooled
  2. customtriturated with methanol (50 mL)
  3. filtrationThe solid precipitate was filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-fa87dad73ed14bc492504bd174026490
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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