Acetic Acid → HCID 135838170, compound

HRID 2289237Notes

Reaction equation

HRID 2289237 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

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 mixure 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, washid 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 9, 58%) 1H NMR(DMSO-d61 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 C1-4H13N3 02.1/2HOAc.1/10H2O: C, 62.75; H, 5.34; N, 14.64. Found C, 62.74; H, 5.31; N, 14.64.

Workup

  1. temperatureheated at 650 C under a nitrogen atmosphere for 4 hours
  2. temperatureAfter cooling
  3. customall solvent was removed under reduced pressure
  4. customThe residue was triturated with water (20 ml)
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-bfb89ca7008b4e77acf9444fedf355cb
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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