Acetic Acid → HCID 135838170, compound

HRID 1883996Notes

Reaction equation

HRID 1883996 reaction equation
Br[CH2:2][C:3]1[C:4]2[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=2[C:6]2[C:7](=[O:20])[NH:8][C:9]([NH:13]C(=O)C(C)(C)C)=[N:10][C:11]=2[CH:12]=1.[C:25](O)(=[O:27])C>C[O-].[Na+]>[NH2:13][C:9]1[NH:8][C:7](=[O:20])[C:6]2[C:5]3[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=3[C:3]([CH2:2][O:27][CH3:25])=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135838176HCID 135838176, compound

Product 1

HCID 135838170HCID 135838170, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
650 °C

Procedure

A solution of N-(6-(bromomethyl)-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.28 g, 0.72 mmole) in 0.3 M sodium methoxide (25 ml) was stirred and heated at 650° C. under a nitrogen atmosphere for 4 hours. After cooling, the mixture was acidified to pH 6 with glacial acetic acid, and then all solvent was removed under reduced pressure. The residue was triturated with water (20 ml), then filtered, washed with water and acetone, and dried to give 3-amino-6-(methoxymethyl)benzo[f]quinazolin-1(2H)-one as an off-white solid. (0.12 g, 58%) 1H NMR (DMSO-d6, 200 MHz) d 3.39 (s, 3H, OCH3); 4.85 (s, 2H, CH2); 6.54 (br s, 2H, NH2); 7.33 (s, 1H, Ar); 7.44 (dt, J=6.9, 1.4 Hz, 1H, Ar); 7.59 (dt, J=6.9, 1.4 Hz, 1H, Ar); 7.96 (dd, J=8.2, 1.0 Hz, 1H, Ar); 9.69 (d, J=8 Hz, 1H, Ar); 11.11 (br s, 1H, NH); 11.91 (br s, <1H, pyr-NH+). Anal. Calculated for C14H13N3O2.1/2HOAc.1/10H2O: C, 62.75; H, 5.34; N, 14.64. Found C, 62.74; H, 5.31; N, 14.64.

Workup

  1. temperatureAfter cooling
  2. customall solvent was removed under reduced pressure
  3. customThe residue was triturated with water (20 ml)
  4. filtrationfiltered
  5. washwashed with water and acetone
  6. customdried

Sources & evidence

ORD record
ord-64a311883f724ed4844fc865029eaa6b
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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